Synfacts 2008(2): 0132-0132  
DOI: 10.1055/s-2007-992456
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Enzymatic One-Pot Synthesis of Iminocyclitols

Contributor(s): Victor Snieckus, Wei Gan
M. Sugiyama, Z. Hong, P.-H. Liang, S. M. Dean, L. J. Whalen, W. A. Greenberg*, C.-H. Wong*
the Scripps Research Institute, La Jolla, USA
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23. Januar 2008 (online)


A one-pot synthesis of polyhydroxy­lated pyrrolidines and piperidines, usually called iminocyclitols, by using fructose-6-phosphate aldolase (FSA) as biocatalyst is reported. When racemic aldehydes A are used, the reactions are selective for (R)-aldehydes. Analysis of a piperidine product shows complete diastereoselectivity and 93% enantioinduction. The detailed analysis of the enantioselectivity and diastereoselectivity of these FSA-catalyzed reactions is under further study.