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DOI: 10.1055/s-0029-1218769
A Rapid Access to (±)-Sedamine and Some Original N-Benzyl Unsaturated Analogues
Publication History
Publication Date:
05 May 2010 (online)
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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- Supporting Information
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References
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].