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Note | Regular issue | Vol 55, No. 8, 2001, pp.1591-1597
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9271
Diastereoselective Synthesis of trans-N-Benzyl-2-(2-methylphenyl)-6-phenyl-4-piperidone

Kaori Ishimaru* and Takakazu Kojima

*Department of Chemistry, The National Defense Academy, 1-10-20 Hashirimizu, Yokosuka 239-8686, Japan


Diastereoselective synthesis of trans-N-benzyl-2-(2-methylphenyl)-6-phenyl-4-piperidone (6a) was performed by cycloaddition of the aldimine (1c) with 2-silyloxy-1,3-butadiene in the presence of trimethylsilyl triflate. The use of the p-trimethylsilyl substituent of the aromatic ring of the aldimine gave high diastereoselectivity of the product.