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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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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cited_by cdi_FETCH-LOGICAL-a381t-2e5454afb5e75fb3ae0886364e78b571a059c0dbde0080e72079f129f975e2ae3
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description 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.
doi_str_mv 10.1021/jo051029u
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Benzaldehydes - chemistry
Chemistry
Exact sciences and technology
Nitriles - chemical synthesis
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
title New Strategy for the Asymmetric Synthesis of Phenyl Ketone Cyanohydrins:  Quaternization of Cyanohydrins Derived from 2-p-Tolylsulfinyl Benzaldehyde
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