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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 - J. Org. Chem. (2014)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry and Biochemistry, University of San Diego , 5998 Alcala Park, San Diego, California 92110, United States.

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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Acid-Mediated Elimination of Alcohol 3
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sch3: Acid-Mediated Elimination of Alcohol 3


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 - J. Org. Chem. (2014)

Acid-Mediated Elimination of Alcohol 3
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4120978&req=5

sch3: Acid-Mediated Elimination of Alcohol 3
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry and Biochemistry, University of San Diego , 5998 Alcala Park, San Diego, California 92110, United States.

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.

Show MeSH