Gold(I)-Catalyzed Stereoselective Olefin Cyclopropanation

A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)−carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinyl cyclopropanes w...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-12, Vol.127 (51), p.18002-18003
Main Authors: Johansson, Magnus J, Gorin, David J, Staben, Steven T, Toste, F. Dean
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Catalysis
Chemistry
Cyclization
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Exact sciences and technology
Gold - chemistry
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Stereoisomerism
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Summary:A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)−carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to 94% ee) preparation of vinyl cyclopropanes with high cis-selectivity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0552500