title: Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes.
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.
authors.affiliation: Department of Organic Chemistry, University of Geneva, 30, quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Belot
authors.forename: Assunta
authors.initials: A
authors.lastname: Massaro
authors.forename: Alice
authors.initials: A
authors.lastname: Tenti
authors.forename: Alessandro
authors.initials: A
authors.lastname: Mordini
authors.forename: Alexandre
authors.initials: A
authors.lastname: Alexakis