Review

. 2023 Oct 25;123(20):11817-11893.

doi: 10.1021/acs.chemrev.3c00059. Epub 2023 Oct 4.

Metal-Catalyzed Enantioconvergent Transformations

Miguel Yus¹, Carmen Nájera¹, Francisco Foubelo^{1

2}, José M Sansano^{1

2}

Affiliations

¹ Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.
² Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.

PMID: 37793021
PMCID: PMC10603790
DOI: 10.1021/acs.chemrev.3c00059

Review

Metal-Catalyzed Enantioconvergent Transformations

Miguel Yus et al. Chem Rev. 2023.

. 2023 Oct 25;123(20):11817-11893.

doi: 10.1021/acs.chemrev.3c00059. Epub 2023 Oct 4.

Authors

Miguel Yus¹, Carmen Nájera¹, Francisco Foubelo^{1

2}, José M Sansano^{1

2}

Affiliations

¹ Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.
² Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.

PMID: 37793021
PMCID: PMC10603790
DOI: 10.1021/acs.chemrev.3c00059

Abstract

Enantioconvergent catalysis has expanded asymmetric synthesis to new methodologies able to convert racemic compounds into a single enantiomer. This review covers recent advances in transition-metal-catalyzed transformations, such as radical-based cross-coupling of racemic alkyl electrophiles with nucleophiles or racemic alkylmetals with electrophiles and reductive cross-coupling of two electrophiles mainly under Ni/bis(oxazoline) catalysis. C-H functionalization of racemic electrophiles or nucleophiles can be performed in an enantioconvergent manner. Hydroalkylation of alkenes, allenes, and acetylenes is an alternative to cross-coupling reactions. Hydrogen autotransfer has been applied to amination of racemic alcohols and C-C bond forming reactions (Guerbet reaction). Other metal-catalyzed reactions involve addition of racemic allylic systems to carbonyl compounds, propargylation of alcohols and phenols, amination of racemic 3-bromooxindoles, allenylation of carbonyl compounds with racemic allenolates or propargyl bromides, and hydroxylation of racemic 1,3-dicarbonyl compounds.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

**Figure 1**
Conversion of racemates into a single enantiomer.

**Scheme 1. Enantioconvergent Ni-Catalyzed Kumada Reactions of α-Bromoketones 1 and 4 with Arylmagnesium Halides**

**Scheme 2. Enantioconvergent Co-Catalyzed Kumada Reactions of α-Bromo Esters 7 with Arylmagnesium Bromide**

**Scheme 3. Enantioconvergent Co-Catalyzed Kumada Reaction of α-Bromo Esters 7 with Alkenyl Grignard Reagents**

**Scheme 4. Enantioconvergent Fe-Catalyzed Kumada Reactions of α-Chloro and α-Bromo Esters 7 with Arylmagnesium Bromides**

**Scheme 5. Enantioconvergent Ni-Catalyzed Negishi Reactions of α-Bromo Amides 18 and Benzylic Halides 21 and 23 with Alkylzinc Reagents**

**Scheme 6. Enantioconvergent Ni-Catalyzed Negishi Reaction of Chloroindane 27 with Alkylzinc 28**

**Scheme 7. Enantioconvergent Ni-Catalyzed Negishi Reactions of Benzylic Mesylates with Arylzinc Reagents**

**Scheme 8. Enantioconvergent Ni-Catalyzed Negishi Reactions of α-Bromo Ketones 1, α-Bromo Nitriles 36, and α-Bromo-α-fluoro Ketones 39 with Aryl and Alkenylzinc Reagents**

**Scheme 9. Enantioconvergent Ni-Catalyzed Negishi Reactions of α-Bromoalkyl Sulfonamides 42 and Sulfones 43, as Well as CF₃–Substituted Alkyl Bromides 44 with Arylzinc Reagents**

**Scheme 10. Enantioconvergent Ni-Catalyzed Negishi Reactions of α-Haloboronates 48 and α-Halosilanes 51 and 54 with Alkylzinc Bromides**

**Scheme 11. Enantioconvergent Ni-Catalyzed Negishi Reaction of α-Phthalimido Alkyl Chlorides 57 or N-Hydroxyphthalimide Esters 58 of Protected α-Amino Acids with Alkylzinc Iodides**

**Scheme 12. Enantioconvergent Ni-Catalyzed Negishi Reactions of α-Chloro Glycinates 62 with Alkylzinc Iodides**

**Scheme 13. Enantioconvergent Co-Catalyzed Negishi Reactions of α-Bromo Esters 7 with Arylzinc Bromides**

**Scheme 14. Enantioconvergent Co-Catalyzed Negishi Reactions of Benzyl Chlorides 70 with Arylzinc Reagents**

**Scheme 15. Enantioconvergent Ni-Catalyzed Suzuki Reactions of Homobenzylic Bromides 72 with Alkylboranes 73**

Scheme 16. Enantioconvergent Ni-Catalyzed Suzuki Reactions of β-Halogenated Compounds: Reaction of Acylated Halohydrins 76, β-Chloro Alkylanilines 77, and N-Protected β-Bromoalkylamines 78 and 83 with Alkylboranes 73

**Scheme 17. Enantioconvergent Ni-Catalyzed Suzuki Reactions of γ-Halogenated Sulfonamide 86, Sulfones 87, and Carboxamides 88 with Alkylboranes 73**

**Scheme 18. Enantioconvergent Ni-Catalyzed Suzuki Reactions of 1-Halo-1-fluoroalkanes 92, 95, and 97 with Alkylboranes 73**

Scheme 19. Enantioconvergent Ni-Catalyzed Suzuki Reactions of α-Bromobenzyl Trifluoromethyl Ethers 99 with Aryl Pinacol Boronates **100**

**Scheme 20. Enantioconvergent Ni-Catalyzed Arylation of Fluorinated Benzylic Bromides 44, **103**, and **104** with Lithium Organoboronates **100** and ZnBr₂**

**Scheme 21. Enantioconvergent Co-Catalyzed Arylation of Fluorinated Secondary Benzyl Bromides **112** with Lithium Aryl n-Butyl Pinacol Boronates **100** and ZnBr₂**

**Scheme 22. Enantioconvergent Ni-Catalyzed Suzuki Reaction of 2-Bromophthalides **118** with Arylboronic Acids**

**Scheme 23. Enantioconvergent Ni-Catalyzed Suzuki Reactions of Spiroepoxyindoles **121** with Alkenylboronic Acids**

Scheme 24. Enantioconvergent Co-Catalyzed Suzuki Reactions of Spiroepoxyoxindoles **121** with Potassium Allyltrifluoroborate **124**

Scheme 25. Enantioconvergent Fe-Catalyzed Suzuki Reaction of t-Butyl α-Bromopropionate 7 with Lithium Aryl Pinacol Boronates **100**

Scheme 26. Enantioconvergent Iron-Catalyzed Suzuki Reactions of Benzylic Chlorides 70 with Arylboronic Pinacol Esters **128**

**Scheme 27. Enantioconvergent Cu-Catalyzed Suzuki Reactions of Benzylic Bromides 23 with Aryl and Alkenyl Boronates **131** and **133**, Respectively**

**Scheme 28. Enantioconvergent Cu-Catalyzed Suzuki Reaction of α-Bromo-β-lactams **136** with Aryl and Alkenyl Boronates **137** and **138**, Respectively**

**Scheme 29. Enantioconvergent Ni-Catalyzed Hiyama Reactions of α-Bromo Esters 7 with Aryl or Alkenylsiloxanes**

**Scheme 30. Enantioconvergent Ni-Catalyzed Hiyama Reactions of α-Chloro-α-trifluoromethyl Methyl Ethers **141** with Aryl or Alkenyl Siloxanes**

**Scheme 31. Enantioconvergent Ni-Catalyzed Cross-Coupling Reactions of Secondary Benzyl Bromides 21 and 23 with Alkynylindium Reagents**

**Scheme 32. Enantioconvergent Ni-Catalyzed Cross-Coupling Reactions of α-Bromo Ketones 1 and α-Bromo Sulfonamides 42 and Sulfones 43 with Alkenylzirconium Reagents**

**Scheme 33. Enantioconvergent Ni-Catalyzed Cross-Coupling Reactions of Tertiary Alkyl Halides **152** and **158** with Alkenylzirconium Reagents**

**Scheme 34. Enantioconvergent Ni- and Pd-Catalyzed Cross-Coupling of Secondary Benzylic Bromides 23 with Alkynyl and Alkenylaluminum Reagents, Respectively**

**Scheme 35. Enantioconvergent Ni-Catalyzed Cross-Coupling Reactions of α-Trifluoromethyl-α-bromomethyl Thioethers **164** with Aryltitanium(IV) Reagents**

Scheme 36. Enantioconvergent Photoreduced Cu-Catalyzed N-Alkylation of Carbazoles and Indoles with α-Chloro Amides **166**

**Scheme 37. Enantioconvergent Photoinduced Cu-Catalyzed N-Alkylation of Carboxamides with γ-Bromo Phosphonates **170**, Amides **173**, Esters **174**, Ketones **175**, and Sulfones 87**

Scheme 38. Enantioconvergent Photoinduced Cu-Catalyzed N-Alkylation of Anilines with α-Chloro Nitriles **180** and α-Halo Carboxamides **183**

**Scheme 39. Enantioconvergent Cu-Catalyzed N-Alkylation of Secondary Benzylic Bromides 23, α-Bromo Ketones 1, α-Bromo Amides 18, and α-Bromo Nitrile 36 with Sulfoximines**

**Scheme 40. Enantioconvergent Cu-Catalyzed N-Alkylation of α-Chloro Amides **191** and **166** with Aliphatic Amines and Ammonia**

**Scheme 41. Enantioconvergent Cu-Catalyzed Cross-Coupling of α-Halo Amides **191** with Oxygen Nucleophiles**

**Scheme 42. Enantioconvergent Cu-Catalyzed Michaelis–Becker Reaction of Alkyl Halides with H-Phosphonates**

**Scheme 43. Enantioconvergent Strategy for Cu-Catalyzed Radical C(sp³)–C Cross-Coupling Reactions**

**Scheme 44. Enantioconvergent Photocatalyzed Cu-Catalyzed Cyanation of Esters **210** and **212** with TMSCN**

Scheme 45. Enantioconvergent Cu-Catalyzed Cyanation of Cyclopentanone and Cyclobutanone Oxime Esters **214** and **216** with TMSCN to Give Dinitriles **215** and **217**

**Scheme 46. Enantioconvergent Cu-Catalyzed Reaction of Secondary Benzylic Bromides 23 with Acetylenes**

**Figure 2**
TSs for the Cu-catalyzed cross-coupling of secondary and tertiary radicals with acetylenes.

**Scheme 47. Enantioconvergent Cu-Catalyzed Sonogashira–Hagihara Reaction of Tertiary α-Halo Amides **183** and **136** with Acetylenes**

Scheme 48. Enantioconvergent Photocatalytic and Copper-Catalyzed Decarboxylative Alkynylation of Esters **210**

**Scheme 49. Enantioconvergent Cu-Catalyzed Sonogashira–Hagihara Reaction of α-Bromo Amides 18 with Acetylenes**

**Scheme 50. Enantioconvergent Ni-Catalyzed Reaction of α-Bromo Amides 18 with Nitroalkanes**

**Scheme 51. Enantioconvergent Ni-Catalyzed Miyaura Borylation of Benzylic Chlorides 70**

**Scheme 52. Enantioconvergent Cu-Catalyzed Miyaura Borylation of Benzylic Chlorides 70**

**Scheme 53. Enantioconvergent Ni-Catalyzed Negishi Reactions of Racemic α-Zincated N-Boc-pyrrolidine 231 with Alkyl Halides**

**Scheme 54. Enantioconvergent Ni-Catalyzed Negishi Reaction of Racemic β-Zincated Amides **233** with Alkyl Iodides**

Scheme 55. Doubly Enantioconvergent Ni-Catalyzed Negishi Reaction of α-Zincated N-Boc-pyrrolidine **231** with Racemic Alkyl Electrophiles **236**

**Scheme 56. Enantioconvergent Photocatalytic and Ni-Catalyzed Suzuki Reactions of Potassium Alkyltrifluoroborate **238** with Aryl Bromides**

**Figure 3**
Proposed mechanisms for conventional reductive cross-coupling reactions.

**Scheme 57. Enantioconvergent Ni-Catalyzed Reductive Acyl Cross-Coupling of Benzylic Chlorides 70**

**Scheme 58. Enantioconvergent Ni-Catalyzed Reductive Cross-Coupling of Benzylic Chlorides 70 with Alkenyl Bromides**

**Scheme 59. Enantioconvergent Ni-Catalyzed RCC of Chloro(arylmethyl)silanes **241** with Alkenyl Bromides**

**Scheme 60. Enantioconvergent Ni-Catalyzed RCC of α-Chloro Sulfones **243** with Alkenyl Bromides**

**Scheme 61. Enantioconvergent Ni-Catalyzed Reductive Decarboxylative Cross-Coupling of N-Hydroxyphthalimide Esters **210** with Alkenyl Bromides**

**Scheme 62. Enantioconvergent Ni-Catalyzed Reductive Cross-Coupling of α-Chloro Nitriles **246** and Benzylic Chlorides 70 with Aryl Iodides**

**Scheme 63. Enantioconvergent Ni-Catalyzed Reductive Cross-Coupling of Styryl Aziridine **249** with Aryl Iodides**

**Scheme 64. Enantioconvergent Ni-Catalyzed Reductive Cross-Coupling of α-Chloro Sulfones **243** with Aryl Halides**

**Scheme 65. Enantioconvergent Ni-Catalyzed Reductive Cross-Coupling of α-Chloro Esters **251** with Aryl Iodides**

**Scheme 66. Enantioconvergent Photoredox and Ni-Catalyzed Decarboxylative Cross-Coupling of α-Amino Acids and Aryl Bromides**

Scheme 67. Enantioconvergent Photoredox and Ni-Catalyzed Decarboxylative Cross-Coupling of α-Heterocyclic Carboxylic Acids **254**

Scheme 68. Enantioconvergent Rh-Photocatalyzed Decarboxylative Cross-Coupling of N-Aryl Glycines and α-Chloro Imidazol-2-yl Ketones **257**

**Scheme 69. Enantioconvergent Photoredox/Ni-Catalyzed Acyl–Akyl Cross-Coupling of 4-Alkyl-1,4-dihydropyridines **260** and **261** with Anhydrides**

**Scheme 70. Enantioconvergent Photoredox/Ni-Catalyzed Reductive Cross-Coupling of α-Chloro Esters **251** with Aryl Iodides**

**Scheme 71. Enantioconvergent Photoredox Ni-Catalyzed Reductive Cross-Coupling of α-Chloroboranes 48 with Aryl Iodides**

**Scheme 72. Enantioconvergent Photoredox/Ni-Catalyzed Reductive Cross-Coupling of α-CF₃-Substituted Alkyl Bromides 44 with Aryl Iodides**

**Scheme 73. Enantioconvergent Photoredox/Ni-Catalyzed Reductive Cross-Coupling of Styrene Oxides with Aryl Iodides**

**Scheme 74. Enantioconvergent Photoredox Ni-Catalyzed Reductive Cross-Coupling of α-Bromophosphonates **265** with Aryl Iodides**

**Scheme 75. Enantioconvergent Ni-Catalyzed Negishi Reaction of Allylic Chlorides **266** with Alkylzinc Reagents**

**Scheme 76. Enantioconvergent Ni-Catalyzed Negishi Reaction of Silylated Allylic Halides **269** and **270** with Alkylzinc Bromides**

**Scheme 77. Enantioconvergent Ni-Catalyzed Suzuki Cross-Coupling of 2-Ethoxy-1,2-dihydroquinolines **273** with Arylboroxines**

**Scheme 78. Enantioconvergent Ni-Catalyzed Negishi Reactions of Propargylic Bromides **202** and Carbonates **276** with Arylzinc Reagents**

**Scheme 79. Enantioconvergent Ni-Catalyzed Negishi Reaction of α-Silylated Propargylic Bromides **277** with Primary Alkylzinc Reagents**

**Scheme 80. Enantioconvergent Cu-Catalyzed Suzuki Reactions of Propargylic Bromides **202** with Aryl and Alkenyl Boronates **131** and **133**, Respectively**

Scheme 81. Enantioconvergent Photoredox Cu-Catalyzed Cyanation of Propargylic Esters **281**

Scheme 82. Enantioconvergent Cu-Catalyzed Cross-Coupling of Benzylic Bromides 23 with Azoles **283**–**285**

Scheme 83. Enantioconvergent Photo- and Cu-Catalyzed Cross-Coupling of Benzylic Bromides 23 with Oxazoles **284** and **285**

**Scheme 84. Enantioconvergent Ir-Catalyzed Annulation of 3-Aryl-3-hydroxyisoindolin-1-ones **291** with 1,3-Dienes**

**Scheme 85. Enantioconvergent Rh-Catalyzed Annulation of 4-Aryl-5-pyrazolones **296** with Alkynes**

Scheme 86. Enantioconvergent Ni-Catalyzed α-Arylation of Cyclic Ketones **299** with Aryl Pyrimidyl Ethers **300**

Scheme 87. Enantioconvergent Ni-Catalyzed Reaction of 3-Bromooxindoles **303** with 3-Substituted N-Boc Oxindoles **304**

Scheme 88. Enantioconvergent Ni-Catalyzed α-Arylation of Secondary Benzylic Alcohols 30 with Arylboronates **137**

Scheme 89. Enantioconvergent Cu/CPA-Catalyzed β-Amination of Hydrazones **311** Derived from Ketones **309**

Scheme 90. Enantioconvergent Co-Catalyzed γ-Amination of Sulfamoyl Azides **315**

**Scheme 91. Pd-Catalyzed Allylic C–H Functionalization**

**Figure 4**
Asymmetric strategies in the Pd-catalyzed allylic C–H functionalization.

**Scheme 92. Enantioconvergent Pd-Catalyzed Allylic Alkylation of 1,3-Diketones **318** with Allylbenzenes**

Scheme 93. Enantioconvergent Pd-Catalyzed Allylic Alkylation of 1,4-Dienes with Cyclic β-Keto Esters **321**

**Scheme 94. Enantioconvergent Pd-Catalyzed Allylic Alkylation of Azlactones **324** with 1,4-Dienes**

**Scheme 95. Enantioconvergent Pd- and CPA-Catalyzed Allylic Alkylation of Aldehydes **327** with Terminal Alkenes**

**Scheme 96. Enantioconvergent Pd- and CPA-Catalyzed Allylic Alkylation of Pyrazol-5-ones **296** with Terminal Alkenes**

**Scheme 97. Enantioconvergent Pd- and Achiral Phosphoric Acid-Catalyzed Allylic Alkylation of Pyrazol-5-ones **296** with 1,4-Dienes**

**Scheme 98. Enantioconvergent Pd- and Achiral Phosphoric Acid-Catalyzed Allylic Alkylation of 5H-Thiazol-4-ones **338** and **341** with 1,4-Dienes**

Scheme 99. Enantioconvergent Ni-Catalyzed Hydroalkylation of Olefins with α-Bromo Amides 18 and **136**

**Scheme 100. Enantioconvergent Ni-Catalyzed Hydroalkylation of Alkenes with α-Bromo Amides 18**

Scheme 101. Enantioconvergent Ni-Catalyzed Hydroalkylation of Olefins with α-Heteroatom Phosphorus and Sulfur Alkyl Bromides **347**

Scheme 102. Enantioconvergent Ni-Catalyzed Hydroalkylation of Alkenes with α-Bromo O-Acyl Alcohols **349**

Scheme 103. Enantioconvergent Pd-Catalyzed Hydroalkylation of (E)-1-Phenyl-1,3-butadiene with t-Butyl α-Cyanopropionate **351**

Scheme 104. Enantioconvergent Pd-Catalyzed Hydroalkylation of 1-Benzyloxyallenes with Azlactones **324**

Scheme 105. Enantioconvergent Pd-Catalyzed Hydroalkylation of 1-Alkoxyallenes with 3-Substituted Oxindoles **304**

Scheme 106. Enantioconvergent and Regiodivergent Pd- and CPA-Catalyzed Hydroalkylation of 1-Alkoxyallenes with Pyrazolones **296**

**Scheme 107. Enantioconvergent Au(I)- and Enamine-Catalyzed Hydroalkylation of Allenamides **360**, **365**, and **366** with Aldehydes**

**Scheme 108. Enantioconvergent Pd- and Amine-Catalyzed Hydroalkylation of Allenes with β-Keto Carbonyl Compounds and Aldehydes**

**Scheme 109. Enantioconvergent Ni-Catalyzed Hydroalkylation of Alkynes with α-Bromo Amides 18**

**Scheme 110. Enantioconvergent and Stereodivergent Rh- and Amine-Catalyzed Hydroalkylation of Alkynes with Aldehydes**

**Scheme 111. Hydrogen Autotransfer Catalysis**

**Scheme 112. Enantioconvergent Ir- and CPA-Catalyzed Amination of Alcohols 30 by Hydrogen Autotransfer**

**Scheme 113. Enantioconvergent Ru-Catalyzed Amidation of 1,2-Diols by Hydrogen Autotransfer**

**Scheme 114. Enantioconvergent Ni-Catalyzed Amination of Alcohols 30 by Hydrogen Autotransfer**

**Scheme 115. Enantioconvergent Ir- and CPA-Catalyzed Intramolecular Amination of Amino Alcohols **384** by Hydrogen Autotransfer**

**Scheme 116. Enantioconvergent Iridium- and Zn(OTf)₂-Catalyzed Epoxide Opening/Intramolecular Amination with *ortho-*Diamines **388** by Hydrogen Autotransfer**

**Scheme 117. Enantioconvergent Ru-Catalyzed Monoamination of 1,2-Diols by Hydrogen Autotransfer**

**Scheme 118. Enantioconvergent Ir- and CPA-Catalyzed Diamination of 1,2-Diols by Hydrogen Autotransfer**

Scheme 119. Enantioconvergent Ir- and CPA-Catalyzed Indolization/Substitution of Alkynyl Anilines **395**

**Scheme 120. Enantioconvergent Ir-Catalyzed Alkylation of Ketones **399** with Alcohols by Hydrogen Autotransfer**

**Scheme 121. Enantioconvergent Ru-Catalyzed Guerbet Reaction of Secondary Alcohols with Primary Alcohols**

**Scheme 122. Enantioconvergent Ru-Catalyzed Guerbet Reaction of Secondary Alcohols with Primary Ones**

**Scheme 123. Enantioconvergent Ir-Catalyzed Diastereoselective Crotylation of Primary Alcohols or Aldehydes**

Scheme 124. Enantioconvergent Ir-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates **409**

**Scheme 125. Enantioconvergent Ir-Catalyzed Diastereoselective (α-Cyclopropyl)allylation of Primary Alcohols or Aldehydes**

**Scheme 126. Enantioconvergent Ir-Catalyzed Diastereoselective *tert*-(Hydroxy)prenylation of Primary Alcohols or Aldehydes**

**Scheme 127. Enantioconvergent Ir-Catalyzed Diastereoselective Coupling of Vinyl Aziridine **414** with Alcohols, Aldehydes, or 1,3-Diols**

Scheme 128. Enantioconvergent Ni-Catalyzed Diastereoselective Reductive Allylation of Benzaldehyde with Allylic Carbonates **420**

Scheme 129. Enantioconvergent Co-Catalyzed Diastereoselective Reductive Allylation of Aldehydes with Allylic Alcohol Derivatives **421** and **423**

**Scheme 130. Enantioconvergent Cu-Catalyzed Etherification of Propargylic Carbonates **425** with Alcohols and Phenols**

**Scheme 131. Enantioconvergent Cu/Borinic Acid-Catalyzed Etherification of Propargylic Carbonates **425** with Diols**

**Scheme 132. Enantioconvergent Cu-Catalyzed Etherification of Propargylic Carbonates **425** with Secondary Aliphatic Alcohols**

Scheme 133. Enantioconvergent Ni/Sodium Carboxylate **435**-Catalyzed Propargylation of N-Hydroxyphthalimides **433** with Propargylic Carbonates **432**

Scheme 134. Enantioconvergent Ni-Catalyzed Amination of 3-Bromooxindoles **262** with Indolines **437**

**Scheme 135. Enantioconvergent Ni-Catalyzed Amination of 3-Bromooxindoles **262** with Anilines**

Scheme 136. Enantioconvergent Ni-Catalyzed Reaction of 3-Bromooxindoles **262** with Silyl Ketene Imines **441**

**Scheme 137. Enantioconvergent Au-Catalyzed Aldol Reaction of Allenolates **444** with Isatins**

Scheme 138. Enantioconvergent Cr-Catalyzed Allenylation of Aldehydes with Propargylic Bromides **447**

**Scheme 139. Enantioconvergent Photocatalyzed and Ni-Catalyzed Aerobic α-Hydroxylation of β-Keto Esters and Amides**

Scheme 140. Enantioconvergent Photocatalyzed and Cu-Catalyzed α-Hydroxylation of β-Keto Esters **450**

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References

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Metal-Catalyzed Enantioconvergent Transformations

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Metal-Catalyzed Enantioconvergent Transformations

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Abstract

Conflict of interest statement

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