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Carbohydr Res. 2013 Jun 7;374:1-7. doi: 10.1016/j.carres.2013.03.020. Epub 2013 Mar 30.

High diastereoselective vinylogous Mannich reaction induced by O-pivaloylated D-galactosylamine as the chiral auxiliary: stereoselective synthesis of 8-arylazocan-2-one.

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  • 1State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.

Abstract

The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl3 as a promoter in THF. (S)-8-(p-Nitrophenyl) azocan-2-one can be stereoselective synthesized from (S) ethyl 7-galactosylamino-7-(p-nitrophenyl)hepta-2,4-dienoate by sequential hydrogenation of the double bond, cyclic lactam formation, and removal of the N-glycosidic auxiliary under basic conditions.

Copyright © 2013 Elsevier Ltd. All rights reserved.

PMID:
23603240
[PubMed - indexed for MEDLINE]
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