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

doi:10.1016/j.tetlet.2006.11.016

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

33 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 language	English (US)
Pages (from-to)	65-68
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2006.11.016
State	Published - 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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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.",

author = "Narina, {Srinivasarao V.} and Kumar, {Talluri Siva} and Shyla George and Arumugam Sudalai",

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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AU - Kumar, Talluri Siva

AU - George, Shyla

AU - Sudalai, Arumugam

N1 - 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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AB - 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.

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

Abstract

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