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Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes

Massaro, Assunta
Tenti, Alice
Mordini, Alessandro
Published in Organic Letters. 2008, vol. 10, no. 20, p. 4557-4560
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.
PMID: 18783235
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BELOT, Sebastian Pascal et al. Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes. In: Organic Letters, 2008, vol. 10, n° 20, p. 4557-4560. https://archive-ouverte.unige.ch/unige:8013

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Deposited on : 2010-06-21

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