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

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

3,4-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 regiosel...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 43; no. 23; pp. 4289 - 4293
Main Authors: Hu, X.Eric, Kim, Nick K, Ledoussal, Benoit, Colson, Anny-Odile
Format: Journal Article
Language:English
Published: Elsevier Ltd 03-06-2002
Subjects:
aziridine
Grignard addition
phosphoramide
piperidine
stereoselectivity and regioselectivity
stereoselectivity and regioselectivity
phosphoramide
aziridine
piperidine
Grignard addition
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Summary:3,4-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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)00639-1