Highly enantioselective direct vinylogous Michael addition of γ-butenolide to enals.

Adrien Quintard, Alice Lefranc, Alexandre Alexakis

Département de chimie organique, Université de Genève, 30 quai Ernest Ansermet, 1211 Genève 4, Switzerland.

Organic letters 2011 Mar 18

filter terms:

An unprecedented and simple direct vinylogous addition of deconjugated butenolide to enals has been developed in excellent stereoselectivities (>95% ee), with Aminal-PYrrolidine (APY) catalyst. This methodology allows for the efficient preparation of complex γ-butenolide from readily available renewable resources. Furthermore, preliminary mechanistic investigations have allowed for the better understanding of the origin of both stereoselectivities and of the observed high reactivities.

Citation

Adrien Quintard, Alice Lefranc, Alexandre Alexakis. Highly enantioselective direct vinylogous Michael addition of γ-butenolide to enals. Organic letters. 2011 Mar 18;13(6):1540-3