Asymmetric Aza-Morita–Baylis–Hillman-Type Reactions: The Highly Enantioselective Reaction between Unmodified α,β- Unsaturated Aldehydes and N-Acylimines by Organo-co-catalysis

Abstrakt

The organo-co-catalytic aza-Morita-Baylis-Hillman (MBH)-type reaction between N-carbamate protected imines and alpha,beta-unsaturated aldehydes has been developed. The organic co-catalytic system of proline and DABCO enables the asymmetric synthesis of the corresponding N-Boc- and N-Cbz-protected beta-amino-alpha,beta-alkylidene-aldehydes in good to high yields and up to 99% ee.

Klíčová slova

• alpha-amido sulfones
• methyl vinyl ketone
• lewis-base organocatalyst
• mannich-type reactions
• boc protected imines
• beta-amino esters
• in-situ
• activated olefins
• henry reaction
• bronsted acid