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.