期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 31, 页码 10521-10527出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201905426
关键词
alkylation; amines; ammonium enolates; palladium; rearrangement
资金
- National Institutes of Health [R01GM121573]
Herein, we report a modular synthetic route to linear and branched homoallylic amines that operates through a sequential one-pot Lewis base/transition-metal catalyzed allylic alkylation/Hofmann rearrangement strategy. This protocol is operationally trivial, proceeds from simple and easily prepared substrates and catalysts, and enables all aspects of regio- and stereoselectivity to be controlled through a conserved experimental protocol. Overall, the high levels of enantio-, regio-, and diastereoselectivity obtained, in concert with the ability to access orthogonally protected or free amines, render this a straightforward and effective approach for the preparation of useful enantioenriched homoallylic amines. We have also demonstrated the utility of the products in the context of pharmaceutical synthesis.
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