Download PDF
Synfacts 2013; 9(1): 0082
DOI: 10.1055/s-0032-1317738
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Fluoroallylboration of Aldehydes

Contributor(s):
Paul Knochel
,
Christoph Sämann
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
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
 PDF Download Permissions and Reprints

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.


#
#


   Permissions and Reprints