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Synthesis 2012(1): 111-119  
DOI: 10.1055/s-0031-1289635
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Lewis Acid Catalyzed Diastereoselective Vinylogous Mannich Reaction Induced by O-Pivaloylated d-Galactosylamine as the Chiral Auxiliary: Stereoselective Synthesis of 6-Arylpiperidin-2-ones

Bing Cuia, Shasha Konga, Guiping Wua, Zhiwei Miao*a,b, Ruyu Chen*a
a State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
Fax: +86(22)23502351; e-Mail: miaozhiwei@nankai.edu.cn;
b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, P. R. of China
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Publication History

Received 23 September 2011
Publication Date:
02 December 2011 (online)

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Abstract

The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-aminocarbonyl derivatives, in the form of (S)-δ-amino-δ-arylpent-2-enoic ester, has been achieved in high yield via a vinylogous Mannich reaction, utilizing poly-O-pivaloylated d-galacosylamine as the chiral auxiliary. (S)-6-p-Tolylpiperidine-2-one can be stereoselectively synthesized from (S)-δ-amino-δ-arylpent-2-enoic ester by sequential hydrogenation of the double bond, cyclic lactam formation, and removal of the N-glycosidic auxiliary under basic conditions.

Key words

vinylogous Mannich reaction - carbohydrate - chiral auxiliary - stereoselective synthesis - 6-arylpiperidin-2-ones

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Crystallographic data for the structural analysis of compound 5b has been deposited at the Cambridge Crystallographic Data Centre under No. CCDC 802525. These data can be obtained free of charge by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.