Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides

A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with β-substituted vinyl sulfones and α,β-unsaturated esters. Reactions afford easily separable mixtures of two e...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-03, Vol.77 (6), p.2893-2900
Main Authors: García Ruano, José Luis, Fernández-Salas, José Antonio, Maestro, M. Carmen
Format: Article
Language:English
Subjects:
Chemistry
Esters
Exact sciences and technology
Fluorides - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
Sulfones - chemistry
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Summary:A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with β-substituted vinyl sulfones and α,β-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure γ-fluorinated γ-phenylsulfones and γ-phenylesters bearing two chiral centers.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300174k