Phosphine-catalyzed anti-carboboration of alkynoates with alkyl-, alkenyl-, and arylboranes.
J Am Chem Soc
; 136(30): 10605-8, 2014 Jul 30.
Article
em En
| MEDLINE
| ID: mdl-25033017
ABSTRACT
We found that trialkylphosphine organocatalysts promoted unprecedented anti-carboboration of alkynoates with alkyl-, alkenyl-, or arylboranes to form ß-boryl acrylates. The regioselectivity of the carboboration across the polar C-C triple bond exhibited inverse electronic demand, with the less electronegative B atom being delivered to the positively charged ß carbon atom. The regioselectivity and the anti stereoselectivity were both complete and robust. In addition, the substrate scope was broad with excellent functional group compatibility.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article