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Synfacts 2009(9): 1041-1041  
DOI: 10.1055/s-0029-1217789
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Epoxidation of Electron-Deficient α,β-Enones

Contributor(s): Benjamin List, Kristina Zumbansen
C. Zheng, Y. Li, Y. Yang, H. Wang, H. Cui, J. Zhang, G. Zhao*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publikationsverlauf

Publikationsdatum:
21. August 2009 (online)

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Significance

Zhao and co-workers report an asymmetric epoxidation of electron-deficient α,β-unsaturated ketones using prolinol 1 as catalyst. Different β,γ-unsaturated α-keto esters, α,β-unsaturated trichloromethyl and α,β-trifluoromethyl ketones were investigated in this reaction. Moreover, the synthetic applicability of the corresponding products is shown in several transformations. Remarkable is the three-step synthesis of
(-)-(5R,6S)-norbalasubramide and (-)-(5R,6S)-­balasubramide.