Catalytic, enantio-and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres

F Manoni, C Cornaggia, J Murray, S Tallon…

Index: Manoni, Francesco; Cornaggia, Claudio; Murray, James; Tallon, Sean; Connon, Stephen J. Chemical Communications, 2012 , vol. 48, # 52 p. 6502 - 6504

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Citation Number: 20

Abstract

Recently, we disclosed the first examples of an enantioselective variant of this process (Scheme 1B). 9 The methodology exploits the aforementioned relative acidity of homophthalic anhydrides such as 6 in conjunction with an ad hoc-designed bifunctional organocatalyst, which we suggested was capable of promoting both enol formation and face-selective addition to the aldehyde electrophile. The process generates bicyclic lactone products such as 8 which ...