Ramachandran PV, * Tafelska-Kaczmarek A, Chatterjee A. Purdue University, West Lafayette, USA
B-(3,3-Difluoroallyl)diisopinocampheylborane for the Enantioselective Fluoroallylboration of Aldehydes.
J. Org. Chem. 2012;
77: 9329-9333
Key words
enantioselective fluoroallylboration - aldehydes - 2,2-
gem-difluorinated homoallylic alcohols
Significance
An enantioselective fluoroallylboration of a variety of aldehydes with B-(3,3-difluoroallyl)diisopinocampheylborane has been disclosed. The resulting 2,2-gem-difluorinated homoallylic alcohols have been obtained in good yield and high enantioselectivity.
Comment
The described reaction proceeds in one pot. After the synthesis of B-(3,3-difluoroallyl)diisopinocampheylborane out of freshly prepared 1,1-difluoroallene, the aldehyde is added directly to the reaction mixture, followed by an oxidative workup.
