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

TitleEnantioselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone via Rh-catalyzed diastereoselective oxidative C-H aminations
Publication TypeJournal Article
Year of Publication2007
AuthorsNarina, SV, Kumar, TSiva, George, S, Sudalai, A
JournalTetrahedron Letter
Volume48
Issue1
Pagination65-68
Date PublishedJAN
Type of ArticleArticle
ISSN0040-4039
Abstract

An efficient enantioselective synthesis of (-)-cytoxazone (1) and (+)-epi-eytoxazone (2) using proline-catalyzed asymmetric alpha-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. (c) 2006 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2006.11.016
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.347
Divison category: 
Chemical Engineering & Process Development