Work

Organocatalyzed Asymmetric Allylic Alkylation Enables Synthesis of Chiral γ-Lactones Bearing Vicinal Tertiary and Quaternary Stereocenters

Year: 2022

Type: article

Abstract: The synthesis of enantioenriched α-aryl-α'-allyl-γ-butyrolactones bearing vicinal tertiary and quaternary stereocenters through organocatalyzed asymmetric allylic alkylation is reported. The process demonstrated that weakly stabilized enolates derived from α-aryl-γ-butyrolactones can undergo regio-, diastereo-, and enantioselective allylation using the proper activation of Morita-Baylis-Hillman (MBH) carbonates.

Source: Organic Letters

DOI: 10.1021/acs.orglett.2c02001

Authors: Morgane Mando, Mathieu Fares, Christelle Kowandy, Fabienne Grellepois, Emmanuel Riguet

Institutions: Centre National de la Recherche Scientifique, Institut de Chimie Moléculaire de Reims, Université de Reims Champagne-Ardenne

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Université de Reims Champagne-Ardenne

OpenAlex ID: W4286002006

FWCI: 1.109

Cites: 20

Cited by: 13

Related to: 10