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- Title
Catalyst-Controlled Switch in Chemo- and Diastereoselectivities: Annulations of Morita-Baylis-Hillman Carbonates from Isatins.
- Authors
Zhan, Gu; Shi, Ming‐Lin; He, Qing; Lin, Wei‐Jia; Ouyang, Qin; Du, Wei; Chen, Ying‐Chun
- Abstract
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-1 H-indene-1,3(2 H)-diones, in exclusive α-regioselectivity. α-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.
- Subjects
ISATIN; CHEMICAL reactions; PHOSPHINE; CATALYSTS; CHIRALITY
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 6, p2187
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201510825