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Highly Enantioselective Michael Addition of Nitroalkanes to Enones and Its Application in Syntheses of (R)-Baclofen and (R)-Phenibut

Xing-Tao Guo, Jie Shen, Feng Sha, Xin-Yan Wu*

*Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China, Email: xinyanwuecust.edu.cn

X.-T. Guo, J. Shen, F. Sha, X.-Y. Wu, Synthesis, 2015, 47, 2063-2072.

DOI: 10.1055/s-0034-1380203 (free Supporting Information)


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Abstract

A chiral primary amine-thiourea catalyst based on dehydroabietic amine enables a highly enantioselective Michael addition of nitroalkanes to α,β-unsaturated ketones to yield γ-nitro ketones with excellent enantioselectivities (up to 99% ee) and in up to 96% yield. This protocol was successfully applied in asymmetric syntheses of (R)-baclofen and (R)-phenibut.

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Key Words

chiral primary amine-thiourea, organocatalysis, enantioselective Michael addition, nitroalkanes, α,β-unsaturated ketones


ID: J66-Y2015