Enantioselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone via Rh-catalyzed diastereoselective oxidative C-H aminations

Srinivasarao V. Narina, Talluri Siva Kumar, Shyla George, Arumugam Sudalai

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32 Scopus citations

Abstract

An efficient enantioselective synthesis of (-)-cytoxazone (1) and (+)-epi-cytoxazone (2) using proline-catalyzed asymmetric α-amino-oxylation of aldehydes followed by Rh-catalyzed diastereoselective oxidative C-H amination as the key steps is described. syn or anti 1,2-aminoalcohols were obtained by Rh-catalyzed intramolecular amidation of the C-H bonds of carbamates or sulfamate esters with good to excellent diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)65-68
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number1
DOIs
StatePublished - Jan 1 2007

Bibliographical note

Funding Information:
N.V.S., T.S.K. and S.G. thank CSIR, New Delhi, for the award of research fellowships. The authors are thankful to Dr. B. D. Kulkarni, Deputy Director, for his support and encouragement.

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