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

Abstract

A highly enantioselective Michael addition of nitroalkanes to α,β-unsaturated ketones was developed. In the presence of a chiral primary amine–thiourea catalyst based on dehydroabietic amine, γ-nitro ketones were obtained 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 with high yields and excellent enantioselectivities.

Key words

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

• References and Notes


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