期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 6, 页码 2147-2151出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510825
关键词
annulations; density-functional calculations; diastereoselectivity; heterocycles; organocatalysis
资金
- NSFC [21125206, 21572135, 21321061]
Regulating both the chemo- and diastereoselectivity, divergently, of a reaction is highly attractive but extremely challenging. Presented herein is a catalyst-controlled switch in the chemo- and diastereodivergent annulation reactions of Morita-Baylis-Hillman carbonates, derived from isatins and 2-alkylidene-1H-indene-1,3(2H)-diones, in exclusive -regioselectivity. -Isocupreine efficiently catalyzed [2+1] reactions to access cyclopropane derivatives, and the diastereodivergent [3+2] annulations were accomplished by employing either a chiral phosphine or a DMAP-type molecule. All reactions exhibited excellent chemoselectivities, and good to remarkable stereoselectivities were furnished, thus leading to a collection of compounds with skeletal and stereogenic diversity. Moreover, DFT computational calculations elucidated the catalyst-based switch in mechanism.
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