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Journal article
Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol
Journal of the American Chemical Society, Vol.141(4), pp.1489-1493
01/30/2019
PMID: 30642168
Web of Science ID: WOS:000457817100017
Abstract
We report the first enantio- and diastereoselective 1,4-addition of butenolides to chromones. Both α,β- and β,γ-butenolide nucleophiles are compatible with the Zn-ProPhenol catalyst, and preactivation as the siloxyfurans is not required. The scope of electrophiles includes a variety of substituted chromones, as well as a thiochromone and a quinolone, and the resulting vinylogous addition products are generated in good yield (31 to 98%), diastereo- (3:1 to >30:1), and enantioselectivity (90:10 to 99:1 er). These Michael adducts allow rapid access to several natural product analogs, and can be easily transformed into a variety of other interesting scaffolds as well.
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Details
- Title
- Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol
- Publication Details
- Journal of the American Chemical Society, Vol.141(4), pp.1489-1493
- Resource Type
- Journal article
- Publisher
- ACS Publications
- Copyright
- © 2019 American Chemical Society
- Identifiers
- WOS:000457817100017; 99381709174306600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English