Enantioselective Fluoroallylboration of Aldehydes

Paul Knochel; Christoph Sämann

doi:10.1055/s-0032-1317738

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Synfacts 2013; 9(1): 0082
DOI: 10.1055/s-0032-1317738

Metal-Mediated Synthesis

Enantioselective Fluoroallylboration of Aldehydes

Rezensent(en):

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

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Publikationsverlauf

Publikationsdatum:
17. Dezember 2012 (online)

Abstract
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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.

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