Synthesis of Alkylidene(gem-Difluorocyclopropanes) from Propargyl Glycolates by a One-Pot Difluorocyclopropenation/Ireland-Claisen Rearrangement Sequence.
作者： Guillaume Ernouf , Jean-Louis Brayer , Benoît Folléas , Jean-Pierre Demoute , Christophe Meyer
关键词: Stereochemistry 、 Chemistry 、 Glycolates 、 Stereocenter 、 Glycolic acid 、 Claisen rearrangement 、 Moiety 、 Chirality (chemistry) 、 Propargyl 、 Ireland–Claisen rearrangement
摘要: A one-pot difluorocyclopropenation/Ireland–Claisen rearrangement sequence applied to readily available propargyl glycolates was developed as a route toward functionalized alkylidene(gem-difluorocyclopropanes). This strategy conveniently avoids the isolation of unstable 3,3-difluorocyclopropenylcarbinyl arising from difluorocyclopropenation. The Ireland–Claisen proceeds with high diastereoselectivity and chirality transfer afford alkylidene(gem-difluorocyclopropanes) incorporating quaternary stereocenter protected glycolic acid moiety, which are useful building blocks for preparation gem-difluorocyclopropanes.
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