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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3057
Title: Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol
Authors: Trost B.M.
Gnanamani, Elumalai
Kalnmals C.A.
Hung C.-I.J.
Tracy J.S.
Published in: Journal of the American Chemical Society
Abstract: We report the first enantio- and diastereoselective 1,4-addition of butenolides to chromones. Both ?,?- and ?,?-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. © 2019 American Chemical Society.
Citation: Journal of the American Chemical Society (2019), 141(4): 1489-1493
URI: https://doi.org/10.1021/jacs.8b13367
http://repository.iitr.ac.in/handle/123456789/3057
Issue Date: 2019
Publisher: American Chemical Society
ISSN: 27863
Author Scopus IDs: 57217139833
35319775800
56716397100
56768679500
56818624200
Author Affiliations: Trost, B.M., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Gnanamani, E., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Kalnmals, C.A., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Hung, C.-I.J., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Tracy, J.S., Department of Chemistry, Stanford University, Stanford, CA 94305, United States
Corresponding Author: Trost, B.M.; Department of Chemistry, Stanford UniversityUnited States; email: bmtrost@stanford.edu
Appears in Collections:Journal Publications [CY]

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