期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 44, 页码 15819-15823出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909596
关键词
1; 4-biselectrophiles; asymmetric catalysis; oxabenzonorbornadienes; phosphorus ylides; rhodium
资金
- Program for the National Natural Science Foundation of China [21672184, 21861042, 21801221]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT17R94]
- Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province, Yunnan Province Government [2018FY001(016)]
- YunLing Scholar of Yunnan Province
The strong binding ability of P-ylides with transition metals limits the utilization of stabilized P-ylide as nucleophiles in asymmetric organometallic catalysis. Herein we describe the first rhodium-catalyzed asymmetric ring-opening reaction of P-ylides utilizing oxabicyclic alkenes as the electrophilic partner. Various P-ylides including ester-, ketone- and amide-style P-ylides are all applicable. This asymmetric reaction occurs through the cleavage of two bridgehead C-O bonds and the formation of two C-C bonds, and oxabenzonorbornadienes are used as 1,4-biselectrophiles, thus providing access to benzonorcaradienes in good yields with high enantioselectivity and perfect diastereoselectivity. The present protocol also constitutes the first highly enantioselective direct catalytic asymmetric cyclopropanation of stabilized P-ylide nucleophiles.
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