期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 22, 页码 6307-6311出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700632
关键词
allylic compounds; asymmetric catalysis; enantioselectivity; isomerization; rhodium
资金
- Collaborative Research and Training Experience (CREATE) program
- Deutsche Forschungsgemeinschaft (DFG) [LO 2065/1-1]
Herein we describe a rhodium-catalyzed enantioselective isomerization of meso-oxabicyclic alkenes to 1,2-naphthalene oxides. These potentially useful building blocks can be accessed in moderate to excellent yields with impressive enantioselectivities. Additionally, experimental findings supported by preliminary computations suggest that ring-opening reactions of bridgehead disubstituted oxabicyclic alkenes proceed through the intermediacy of these epoxides and may point to a kinetically and thermodynamically favored reductive elimination as the origin for the observed enantioselectivities.
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