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Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: Tandem aminoxylation/o-n bond heterolysis reactions

Academic Article
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Overview

authors

  • Ramachary, D. B.
  • Barbas III, Carlos

publication date

  • 2005

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] A practical organocatalytic process for the synthesis of optically active, highly substituted alpha-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.

subject areas

  • Amines
  • Amino Acids
  • Combinatorial Chemistry Techniques
  • Ketones
  • Molecular Structure
  • Nitroso Compounds
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol050245e

PubMed ID

  • 15816756
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Additional Document Info

start page

  • 1577

end page

  • 1580

volume

  • 7

issue

  • 8

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