Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol

Article abstract of DOI:10.1021/jacs.8b13367

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.

Full text of DOI:10.1021/jacs.8b13367

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Communication
Direct Enantio- and Diastereoselective Vinylogous Addition
of Butenolides to Chromones Catalyzed by Zn-ProPhenol
Barry M. Trost, Elumalai Gnanamani, Christopher A. Kalnmals, Chao-I (Joey) Hung, and Jacob S. Tracy
J. Am. Chem. Soc., Just Accepted Manuscript • DOI: 10.1021/jacs.8b13367 • Publication Date (Web): 14 Jan 2019
Downloaded from http://pubs.acs.org on January 14, 2019
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