Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes |
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Authors: | Belot Sébastien Massaro Assunta Tenti Alice Mordini Alessandro Alexakis Alexandre |
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Institution: | Department of Organic Chemistry, University of Geneva, 30, quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland. |
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Abstract: | The asymmetric organocatalyzed Michael addition of aldehydes to alpha,beta-gamma,delta-unsaturated nitro compounds has been accomplished using only 5 mol % of (S)-diphenylprolinol silyl ether and 2 equiv of aldehyde in a mixture of ethanol and water (5% v/v). The Michael adducts were obtained in good yields, diastereoselectivities up to 94/6, and ee's up to 99%. This process provides synthetically useful compounds which can easily lead to more complex molecules, as exemplified with substituted tetrahydropyran or cyclohexene. |
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