Amine-catalyzed direct Diels-Alder reactions of α,β-unsaturated ketones with nitro olefins

Amine-catalyzed Diels Alder reactions of alpha,beta-unsaturated ketones with dienophiles have been developed. Either (S)-1-(2-pyrrolidinylmethyl)pyrrolidine or L-proline catalyzed the in situ-generation and reaction of 2-amino-1,3-dienes to provide cyclohexanone derivatives in good yield (up to 87%) in one step with modest enantioselectivity. (C) 2002 Published by Elsevier Science Ltd.