Gold(I)‐Catalyzed Highly Diastereo‐ and Enantioselective Alkyne Oxidation/Cyclopropanation of 1,6‐Enynes
2014; Wiley; Volume: 53; Issue: 50 Linguagem: Inglês
10.1002/anie.201407717
ISSN1521-3773
AutoresDeyun Qian, Haoxiang Hu, Feng Liu, Bin Tang, Weimin Ye, Yidong Wang, Junliang Zhang,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoA 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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