Journal Articles Tetrahedron: Asymmetry Year : 2010

Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry

Abstract

Over 20 new and easily prepd. diamines were screened for the asym. Morita-Baylis-Hillman reaction. Chiral 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of Me vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivs. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee.

Dates and versions

hal-01020066 , version 1 (07-07-2014)

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Mickael Pouliquen, Jérôme Blanchet, Michaël de Paolis, B. Rema Devi, Jacques Rouden, et al.. Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry. Tetrahedron: Asymmetry, 2010, 21 (11), pp.1511-1521. ⟨10.1016/j.tetasy.2010.04.038⟩. ⟨hal-01020066⟩
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