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. 2016 Sep 2;6(9):6207-6213.
doi: 10.1021/acscatal.6b01886. Epub 2016 Aug 17.

Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates

Affiliations

Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates

J Caleb Hethcox et al. ACS Catal. .
No abstract available

PubMed Disclaimer

Conflict of interest statement

Notes The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Metallacyclic iridium catalysts.
Scheme 1
Scheme 1
Transition-Metal-Catalyzed Asymmetric Allylic Alkylation
Scheme 2
Scheme 2
Iridium-Catalyzed Asymmetric Allylic Alkylation
Scheme 3
Scheme 3
First Report of Diastereo- and Enantioselective Iridium-Catalyzed Allylic Alkylation
Scheme 4
Scheme 4
Allylic Alkylation of Acyclic β-Ketoesters by Stoltz
Scheme 5
Scheme 5
Allylic Alkylation with Acyclic α-Alkoxy Ketones by Hartwig
Scheme 6
Scheme 6
Counterion-Assisted Iridium-Catalyzed Allylic Alkylation of Azlactones by Hartwig
Scheme 7
Scheme 7
Cation Control of Diastereoselectivity in Iridium-Catalyzed Allylic Alkylation of (a) 5H-Oxazol-4-ones 21 and (b) 5H-Thiazol-4-ones 25 by Hartwig
Scheme 8
Scheme 8
Allylic Alkylation of (a) Bicyclic β-Ketoesters 28 and (b) Monocyclic β-Ketoesters 31 by Stoltz
Scheme 9
Scheme 9
Allylic Alkylation of Extended Enolates by Stoltz
Scheme 10
Scheme 10
Allylic Alkylation of Non-Stabilized Enolates by Hartwig
Scheme 11
Scheme 11
Dual-Catalyst-Promoted Allylic Alkylation of Aldehydes by Carreira
Scheme 12
Scheme 12
Proline-Derived Dual Catalysis by Carreira
Scheme 13
Scheme 13
Diastereoablative Allylic Alkylation of 52 by Stoltz

References

    1. Trost BM, Van Vranken DL. Chem Rev. 1996;96:395–422. - PubMed
    2. Trost BM, Crawley ML. Chem Rev. 2003;103:2921–2944. - PubMed
    3. Lu Z, Ma S. Angew Chem, Int Ed. 2008;47:258–297. - PubMed
    1. Milhau L, Guiry PJ. Top Organomet Chem. 2011;38:95–154.
    1. Pretó̂t R, Pfaltz A. Angew Chem, Int Ed. 1998;37:323–325. - PubMed
    2. Hayashi T, Kawatsura M, Uozumi Y. J Am Chem Soc. 1998;120:1681–1687.
    3. You SL, Zhu XZ, Luo YM, Hou XL, Dai LX. J Am Chem Soc. 2001;123:7471–7472. - PubMed
    4. Zheng WH, Sun N, Hou XL. Org Lett. 2005;7:5151–5154. - PubMed
    5. Zheng WH, Zheng BH, Zhang Y, Hou XL. J Am Chem Soc. 2007;129:7718–7719. - PubMed
    6. Liu W, Chen D, Zhu XZ, Wan XL, Hou XL. J Am Chem Soc. 2009;131:8734–8735. - PubMed
    7. Fang P, Ding CH, Hou XL, Dai LX. Tetrahedron: Asymmetry. 2010;21:1176–1178.
    8. Chen JP, Ding CH, Liu W, Hou XL, Dai LX. J Am Chem Soc. 2010;132:15493–15495. - PubMed
    1. Takeuchi R, Kashio M. Angew Chem, Int Ed Engl. 1997;36:263–265.
    1. Janssen JP, Helmchen G. Tetrahedron Lett. 1997;38:8025–8026.

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