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. 2008 Apr 30;130(17):5608-9.
doi: 10.1021/ja800345r. Epub 2008 Apr 4.

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids

Yonggui Chi  1 , Li Guo, Nathan A Kopf, Samuel H Gellman
Affiliations

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids

Yonggui Chi et al. J Am Chem Soc. .

Abstract

Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides beta-substituted-delta-nitroalcohols in nearly optically pure form (96-99% ee). The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected gamma2-amino acids, which are essential for the systematic conformational studies of gamma-peptide foldamers.

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Figures

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References

    1. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. Pergamon Press; Oxford: 1992.

    1. For recent reviews, see: Jarvo ER, Miller SJ. Tetrahedron. 2002;58:2481.Sibi MP, Manyem S. Tetrahedron. 2000;56:8033.Yamaguchi M. In: Comprehensive Asymmetric Catalysis I–III. Jacobsen EN, Pfaltz A, Yamamoto H, editors. Chapter 31.2 Springer-Verlag; Berlin-Heidelberg, Germany: 1999.

    1. For recent reviews, see: Berner OM, Tedeschi L, Enders D. Eur J Org Chem. 2002. p. 1877.Pellissier H. Tetrahedron. 2007;63:9267.Santanu M, Yang JW, Hoffmann S, List B. Chem Rev. 2007;107:5471.

    1. For selected examples, see: Betancort JM, Barbas CF., III Org Lett. 2001;3:3737.Mase N, Thayumanavan R, Tanaka F, Barbas CF., III Org Lett. 2004;6:2527.Mase N, Watanabe K, Yoda H, Takabe K, Tanaka F, Barbas CF., III J Am Chem Soc. 2006;128:4966.Wang W, Wang J, Li H. Angew Chem, Int Ed. 2005;44:1369.Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew Chem, Int Ed. 2005;44:4212.Lalonde MP, Chen YG, Jacobsen EN. Angew Chem, Int Ed. 2005;45:6366.Wiesner M, Revell JD, Wennemers H. Angew Chem, Int Ed. 2008;47:1871.

    1. For selected examples, see: List B, Pojarliev P, Martin HJ. Org Lett. 2001;3:2423.Okino T, Hoashi Y, Takemoto Y. J Am Chem Soc. 2003;125:12672.Xu Y, Córdova A. Chem Commun. 2006:460.

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