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

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.

SUBMITTER: Raghunadh A

PROVIDER: S-EPMC3817507 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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

Raghunadh Akula A More Satish S SS Chaitanya T Krishna TK Kumar Yadla Sateesh YS Meruva Suresh Babu SB Rao L Vaikunta LV Kumar U K Syam UK

Beilstein journal of organic chemistry 20131017

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. ...[more]

PMID: 24204425

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