New Strategy for the Asymmetric Synthesis of Phenyl Ketone Cyanohydrins:  Quaternization of Cyanohydrins Derived from 2-p-Tolylsulfinyl Benzaldehyde

Optically pure functionalized cyanohydrins derived from 1-[2-(p-tolylsulfinyl)phenyl] ethanone can be obtained by the reaction of 2-p-tolylsulfinyl benzaldehyde derived cyanohydrins with bases and further treatment with suitable electrophiles. High yields and excellent stereoselectivities (up to de...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-09, Vol.70 (18), p.7346-7352
Main Authors: García Ruano, José Luis, Martín-Castro, Ana M, Tato, Francisco, Pastor, César J
Format: Article
Language:English
Subjects:
Benzaldehydes - chemistry
Chemistry
Exact sciences and technology
Nitriles - chemical synthesis
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:Optically pure functionalized cyanohydrins derived from 1-[2-(p-tolylsulfinyl)phenyl] ethanone can be obtained by the reaction of 2-p-tolylsulfinyl benzaldehyde derived cyanohydrins with bases and further treatment with suitable electrophiles. High yields and excellent stereoselectivities (up to de >98%) were obtained for these remote 1,4-asymmetric induction processes controlled by a sulfinyl chiral inductor.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051029u