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Synthesis 2010(14): 2456-2462  
DOI: 10.1055/s-0029-1218769
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Rapid Access to (±)-Sedamine and Some Original N-Benzyl Unsaturated Analogues

Anne Boussonnière, Tsiresy Ranaivondrambola, Jacques Lebreton*, Monique Mathé-Allainmat*
Université de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
Fax: +33(2)51125562; e-Mail: Jacques.Lebreton@univ-nantes.fr; e-Mail: Monique.Mathe@univ-nantes.fr;
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Publication History

Received 18 March 2010
Publication Date:
05 May 2010 (online)

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Abstract

Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity.

Key words

hydrides - diastereoselectivity - piperidines - pyridinium - reduction

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14

The diastereoisomeric ratio was determined by GC analysis [Optima 3 column (Macherey-Nagel), 80 ˚C, 1 min, 12 ˚C/min, 250 ˚C, 1 min, 12 ˚C/min, 300 ˚C]: t R = 19.8 min [(±)-10a; 16%); 21.08 min ((±)-9a; 21%); 20.88 and 23.40 min [(±)-7a and (±)-8a, 42% and 21%, respectively].