Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters
Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. 2014. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. The Journal of Organic Chemistry. 79(15), 7199–7204.
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Author
Guan, Weiye;
Michael, Alicia K.ISTA;
McIntosh, Melissa L.;
Koren-Selfridge, Liza;
Scott, John P.;
Clark, Timothy B.
Abstract
The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki–Miyaura coupling reaction to obtain alkenes of known geometry.
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Publishing Year
Date Published
2014-06-10
Journal Title
The Journal of Organic Chemistry
Publisher
American Chemical Society
Volume
79
Issue
15
Page
7199-7204
ISSN
eISSN
IST-REx-ID
Cite this
Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. The Journal of Organic Chemistry. 2014;79(15):7199-7204. doi:10.1021/jo500773t
Guan, W., Michael, A. K., McIntosh, M. L., Koren-Selfridge, L., Scott, J. P., & Clark, T. B. (2014). Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. The Journal of Organic Chemistry. American Chemical Society. https://doi.org/10.1021/jo500773t
Guan, Weiye, Alicia K. Michael, Melissa L. McIntosh, Liza Koren-Selfridge, John P. Scott, and Timothy B. Clark. “Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters.” The Journal of Organic Chemistry. American Chemical Society, 2014. https://doi.org/10.1021/jo500773t.
W. Guan, A. K. Michael, M. L. McIntosh, L. Koren-Selfridge, J. P. Scott, and T. B. Clark, “Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters,” The Journal of Organic Chemistry, vol. 79, no. 15. American Chemical Society, pp. 7199–7204, 2014.
Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. 2014. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. The Journal of Organic Chemistry. 79(15), 7199–7204.
Guan, Weiye, et al. “Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters.” The Journal of Organic Chemistry, vol. 79, no. 15, American Chemical Society, 2014, pp. 7199–204, doi:10.1021/jo500773t.
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