Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Nitrodienes
Organic Letters2008Vol. 10(20), pp. 4557–4560
Citations Over TimeTop 10% of 2008 papers
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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