Direct Amino Acid-Catalyzed Asymmetric Desymmetrization ofmeso-Compounds: Tandem Aminoxylation/O−N Bond Heterolysis Reactions

Ramachary, Dhevalapally B. ; Barbas, Carlos F. (2005) Direct Amino Acid-Catalyzed Asymmetric Desymmetrization ofmeso-Compounds: Tandem Aminoxylation/O−N Bond Heterolysis Reactions Organic Letters, 7 (8). pp. 1577-1580. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/ol050246e

Related URL: http://dx.doi.org/10.1021/ol050246e

Abstract

A practical organocatalytic process for the synthesis of optically active, highly substituted α-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O−N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O−N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:120802
Deposited On:05 Jul 2021 12:00
Last Modified:05 Jul 2021 12:00

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