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Regio- and stereo-controlled copper organometallic addition to a piperidinyl aziridine: synthesis of trans 3-amino-4-alkyl-piperidines

✍ Scribed by X.Eric Hu; Nick K Kim; Benoit Ledoussal; Anny-Odile Colson

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 134 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00639-1

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✦ Synopsis

Piperidinyl aziridine N-phosphonate underwent ring opening in Grignard addition catalyzed by a copper reagent to yield trans 3-amino-4-alkyl-piperidines. The nucleophilic addition occurred trans to the aziridine group and regioselectively at C-4 position of the piperidine ring. The high regioselectivity was rationalized by steric argument based on conformational analysis.

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