B-(3,3-difluoroallyl)diisopinocampheylborane for the enantioselective fluoroallylboration of aldehydes

P Veeraraghavan Ramachandran; Agnieszka Tafelska-Kaczmarek; Anamitra Chatterjee

doi:10.1021/jo300970z

B-(3,3-difluoroallyl)diisopinocampheylborane for the enantioselective fluoroallylboration of aldehydes

J Org Chem. 2012 Oct 19;77(20):9329-33. doi: 10.1021/jo300970z. Epub 2012 Oct 1.

Authors

P Veeraraghavan Ramachandran¹, Agnieszka Tafelska-Kaczmarek, Anamitra Chatterjee

Affiliation

¹ Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu

PMID: 22973971
DOI: 10.1021/jo300970z

Abstract

The fluoroallylboration of aldehydes with B-(3,3-difluoroallyl)diisopinocampheylborane, which was prepared via the hydroboration of 1,1-difluoroallene, provides chiral 2,2-gem-difluorinated homoallylic alcohols in good yields and 91-97% ee.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Allyl Compounds / chemistry*
Boron Compounds / chemistry*
Molecular Structure
Propanols / chemical synthesis*
Propanols / chemistry
Stereoisomerism

Substances

Aldehydes
Allyl Compounds
Boron Compounds
Propanols
allyl alcohol