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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