Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters | Zendy

Weiye Guan | Zendy; Alicia K. Michael | Zendy; Melissa L. McIntosh | Zendy; Liza KorenSelfridge | Zendy; John P. Scott | Zendy; Timothy Clark | Zendy

Open Access

Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters

Author(s) -

Weiye Guan,

Alicia K. Michael,

Melissa L. McIntosh,

Liza KorenSelfridge,

John P. Scott,

Timothy Clark

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo500773t

Subject(s) - chemistry , stereoselectivity , olefin fiber , organic chemistry , selectivity , catalysis , boronic acid , combinatorial chemistry

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research