Journal
ORGANIC LETTERS
Volume 10, Issue 20, Pages 4557-4560Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801772p
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Funding
- Marie-Curie EST Program Indac-Chem [MEST-CT-2005-019780]
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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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