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Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.
J Org Chem. 2014 Aug 01; 79(15):7199-204.JO

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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Authors+Show Affiliations

Guan W
Department of Chemistry and Biochemistry, University of San Diego , 5998 Alcala Park, San Diego, California 92110, United States.
Michael AK
No affiliation info available
McIntosh ML
No affiliation info available
Koren-Selfridge L
No affiliation info available
Scott JP
No affiliation info available
Clark TB
No affiliation info available

MeSH

AlkenesBoronic AcidsCopperKetonesStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24915498

Citation

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, 2014, pp. 7199-204.
Guan W, Michael AK, McIntosh ML, et al. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. J Org Chem. 2014;79(15):7199-204.
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, 79(15), 7199-204. https://doi.org/10.1021/jo500773t
Guan W, et al. Stereoselective Formation of Trisubstituted Vinyl Boronate Esters By the Acid-mediated Elimination of Α-hydroxyboronate Esters. J Org Chem. 2014 Aug 1;79(15):7199-204. PubMed PMID: 24915498.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. AU - Guan,Weiye, AU - Michael,Alicia K, AU - McIntosh,Melissa L, AU - Koren-Selfridge,Liza, AU - Scott,John P, AU - Clark,Timothy B, Y1 - 2014/07/14/ PY - 2014/6/11/entrez PY - 2014/6/11/pubmed PY - 2015/2/13/medline SP - 7199 EP - 204 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 15 N2 - 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24915498/Stereoselective_formation_of_trisubstituted_vinyl_boronate_esters_by_the_acid_mediated_elimination_of_α_hydroxyboronate_esters_ DB - PRIME DP - Unbound Medicine ER -