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Beilstein J Org Chem. 2013 Oct 17;9:2129-36. doi: 10.3762/bjoc.9.250. eCollection 2013.

Synthesis of enantiomerically pure N-(2,3-dihydroxypropyl)arylamides via oxidative esterification.

Author information

  • 1Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Ltd, Miyapur, Hyderabad, 500 049, India.

Abstract

A highly efficient synthesis of enantiomerically pure (S) and (R)-isomers of N-(2,3-dihydroxypropyl)arylamides has been developed with good overall yields in a two step process. The key step involves the ring opening of the chiral epoxide with a nitrogen heterocyclic carbene (NHC) and further rearrangement to chiral N-(2,3-dihydroxypropyl)arylamides in high yields and enantioselectivity. During the reaction, no erosion in chiral purity was observed.

KEYWORDS:

N-(2,3-dihydroxypropyl)arylamide; nitrogen heterocyclic carbenes (NHC); oxidative esterification of aromatic aldehyde

PMID:
24204425
[PubMed]
PMCID:
PMC3817507
Free PMC Article

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