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. 2010 Sep 1;132(34):11908-9.
doi: 10.1021/ja105924f.

Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins

Nathan A Owston  1 , Gregory C Fu
Affiliations

Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins

Nathan A Owston et al. J Am Chem Soc. .

Abstract

A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

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References

    1. For leading references, see: Rudolph A, Lautens M. Angew Chem, Int Ed. 2009;48:2656–2670.

    1. For a report on catalytic asymmetric cross-couplings of unactivated secondary alkyl electrophiles, see: Saito B, Fu GC. J Am Chem Soc. 2008;130:6694–6695.(Suzuki alkylations of homobenzylic bromides).

    1. For reports on catalytic asymmetric cross-couplings of activated secondary alkyl electrophiles, see: Negishi alkylations of α-bromoamides: Fischer C, Fu GC. J Am Chem Soc. 2005;127:4594–4595.Negishi alkylations of 1-haloindanes: Arp FO, Fu GC. J Am Chem Soc. 2005;127:10482–10483.Negishi alkylations of allylic chlorides: Son S, Fu GC. J Am Chem Soc. 2008;130:2756–2757.Hiyama arylations and vinylations of α-bromoesters: Dai X, Strotman NA, Fu GC. J Am Chem Soc. 2008;130:3302–3303.Negishi arylations of propargylic halides: Smith SW, Fu GC. J Am Chem Soc. 2008;130:12645–12647.Couplings of alkynylindiums with benzylic bromides: Caeiro J, Perez Sestelo J, Sarandeses LA. Chem Eur J. 2008;14:741–746.Negishi arylations of α-bromoketones: Lundin PM, Esquivias J, Fu GC. Angew Chem, Int Ed. 2009;48:154–156.Kumada arylations of α-bromoketones: Lou S, Fu GC. J Am Chem Soc. 2010;132:1264–1266.Zirconium Negishi alkenylations of α-bromoketones: Lou S, Fu GC. J Am Chem Soc. 2010;132:5010–5011.Suzuki arylations of α-haloamides: Lundin PM, Fu GC. J Am Chem Soc. ASAP.

    1. For overviews and leading references, see: Glorius F. Angew Chem, Int Ed. 2008;47:8347–8349.(b) Reference 1.

    1. The Suzuki reaction is perhaps the most widely used cross-coupling process. For leading references, see: de Meijere A, Diederich F, editors. Metal-Catalyzed Cross-Coupling Reactions. Wiley–VCH; New York: 2004. Negishi E-i., editor. Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley Interscience; New York: 2002.

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