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Gold(I)‐Catalyzed Highly Diastereo‐ and Enantioselective Alkyne Oxidation/Cyclopropanation of 1,6‐Enynes
Author(s) -
Qian Deyun,
Hu Haoxiang,
Liu Feng,
Tang Bin,
Ye Weimin,
Wang Yidong,
Zhang Junliang
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407717
Subject(s) - cyclopropanation , stereocenter , enantioselective synthesis , cationic polymerization , moiety , chemistry , alkyne , catalysis , quinoline , oxazoline , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
A highly enantioselective oxidative cyclopropanation of 1,6‐enynes catalyzed by cationic Au I /chiral phophoramidite complexes is presented. The new method provides convenient access to densely functionalized bicyclo[3.1.0]hexanes bearing three contiguous quaternary and tertiary stereogenic centers with high enantioselectivity (up to e.r. 98:2). Control experiments suggest that the quinoline moiety of the β‐gold vinyloxyquinolinium intermediate in the reaction plays an important role in promoting good enantioselectivity through a transitional auxiliary effect in the transition state.
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