Download PDF
Synlett 1997; 1997(1): 95-96
DOI: 10.1055/s-1997-691
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
22 March 2004 (online)

  PDF Download  Permissions and Reprints All articles of this category

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