246. S. Belot, A. Massaro, A. Tenti, A. Mordini, A. Alexakis,
     “Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes”
     Org. Lett. 2008, 10, 4557-4560.

The asymmetric organocatalyzed Michael addition of aldehydes to α,β-γ,δ-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.

DOI : 10.1021/ol801772p 

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