title: Highly enantioselective direct vinylogous Michael addition of γ-butenolide to enals.
abstract: 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.
authors.affiliation: Département de chimie organique, Université de Genève, 30 quai Ernest Ansermet, 1211 Genève 4, Switzerland.
authors.forename: Adrien
authors.initials: A
authors.lastname: Quintard
authors.forename: Alice
authors.initials: A
authors.lastname: Lefranc
authors.forename: Alexandre
authors.initials: A
authors.lastname: Alexakis
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C004511:butenolide; D015107:4-Butyrolactone