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Synlett 1997; 1997(1): 95-96
DOI: 10.1055/s-1997-691
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A [3+2] Annulation Procedure for the Synthesis of Bicyclic Methylenepyrrolidines

Masahiro Sadakane, Ruth Vahle, Kerstin Schierle, Doris Kolter, Eberhard Steckhan*
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany, Fax: Int. +228-73-5683, e-mail: steckhan@uni-bonn.de
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Publication Date:
22 March 2004 (online)

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Reactions between 2-chloromethyl-3-trimethylsilyl-1-propene 1 and N-acyliminium ions, which were generated in situ from α-methoxy or α-acetoxy amides 2, give allylic chlorides 3 in good yields and high stereoselectivities. The allylic chlorides 3 were further transformed to bicyclic methylenepyrrolidines 4 which are building blocks for pharmacologically interesting compounds.

N-Acyliminium ions - methylenepyrrolidines - diastereoselective amidoalkylation

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