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Synfacts 2008(7): 0764-0764  
DOI: 10.1055/s-2008-1077823
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Formation of Piperidines by Asymmetric Formal Aza-[3+3] Cycloaddition

Contributor(s): Benjamin List, Steffen Müller
Y. Hayashi*, H. Gotoh, R. Masui, H. Ishikawa
Tokyo University of Science, Japan
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Publikationsdatum:
20. Juni 2008 (online)

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Significance

Diphenylprolinol silyl ethers were found to catalyze the formal aza-[3+3] cycloaddition of α , β-unsaturated aldehydes and enecarbamates. Using catalyst 3 the corresponding piperidine derivatives were obtained in good yields (73-90%) and excellent enantioselectivities (er = 94:6 to 99.5:0.5), equal for both anomers, which were found to be in an equilibrium. The use of the products as synthetic intermediates was also examined.