Journal Article10.1002/ange.201407717
Gold(I)‐Catalyzed Highly Diastereo‐ and Enantioselective Alkyne Oxidation/Cyclopropanation of 1,6‐Enynes
Deyun Qian,Haoji Hu,Feng Liu,Bin Tang,Weimin Ye,Yidong Wang,Junliang Zhang +6 more
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TL;DR: Highly enantioselective oxidative cyclopropanation of 1,6‐enynes catalyzed by Au(I) complexes. Access to densely functionalized bicyclo[3.1.0]hexanes with high enantioselectivity.
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Abstract: Abstract 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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