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Organocatalytic synthesis of N-Phenylisoxazolidin-5-ones and a one-pot synthesis of beta-amino acid esters.

Authors
Type
Published Article
Journal
Organic Letters
1523-7052
Publisher
American Chemical Society
Publication Date
Volume
10
Issue
5
Pages
953–956
Identifiers
DOI: 10.1021/ol800003n
PMID: 18247633
Source
Medline

Abstract

A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.

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