Highly Enantioselective Aza-Baylis–Hillman-Type Reaction of α,β-Unsaturated Aldehydes with In Situ Generated N-Boc- and N-Cbz-Imines

Abstract

An organocatalytic highly enantioselective aza-Baylis-Hillman reaction of alpha,beta-unsaturated aldehydes with in situ generated N-Boc- and N-Cbz-imines is presented. This novel process opens the pathway for the synthesis of beta-amino carbonyl compounds bearing an alpha-alkylidene group under mild and simple conditions.

Keywords

• Aza-Baylis-Hillman reaction
• organocatalysis
• enantioselectivity
• diastereoselectivity
• sulfur
• alpha
• beta-unsaturated aldehydes
• N-Boc- and N-Cbz-Imines