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A. Quintard, A. Lefranc, A. Alexakis,
“Highly Enantioselective Direct Vinylogous Michael Addition of γ-Butenolide to Enals”
Org. Lett. 2011, 13, 1540-1543.
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.
DOI : 10.1021/ol200235j
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