Studies on a New Access to Z-Ethylenic Pseudodipeptides Based on Ring-Closing Metathesis: Obtention and Reductive Cleavage of N-Arylsulfonyl Dihydropyridones

Abstract In the reaction with TERT-butyloxycarbonyl anhydride (Boc 2 O), N-(O-vinylacetyloxy)benzenesulfonyl allylic amines 4A-C undergo concomitant O to N acyl migration to give N-(O-vinyl­acetyloxy)-N-(O-TERT-butoxycarbonyloxy)benzenesulfonyl allylic amines 16A-C. In the presence of Grubbs’ second...

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Published in:Synlett 2009-06, Vol.2009 (10), p.1614-1618
Main Authors: Vandromme, Lucie, N’Guyen Van Buu, Olivier, Guibé, François, Bezzenine-Lafollée, Sophie
Format: Article
Language:English
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Summary:Abstract In the reaction with TERT-butyloxycarbonyl anhydride (Boc 2 O), N-(O-vinylacetyloxy)benzenesulfonyl allylic amines 4A-C undergo concomitant O to N acyl migration to give N-(O-vinyl­acetyloxy)-N-(O-TERT-butoxycarbonyloxy)benzenesulfonyl allylic amines 16A-C. In the presence of Grubbs’ second-generation catalyst, 16A-C are converted into N-arylsulfonyl-3,6-dihydropyridones 17A-C. The Boc group was removed from 17B and the resulting 18 was reductively cleaved with LiAlH 4 to the ring-opened N-arylsulfonylamino alcohol 20 and with DIBAL to the ring-opened N-arylsulfonylamino aldehyde 21 that are close N-protected precursors of the Z-ethylenic pseudopeptidic analogue of L-Phe-Gly.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1217328