A straightforward synthesis of enantiomerically pure trans-2,5-bis(alkyloxymethyl) pyrrolidines by 1,3-dipolar cycloaddition reactions of azomethine ylides

Authors
Wittland, C Risch, N
Citation
C. Wittland et N. Risch, A straightforward synthesis of enantiomerically pure trans-2,5-bis(alkyloxymethyl) pyrrolidines by 1,3-dipolar cycloaddition reactions of azomethine ylides, J PRAK CH C, 342(3), 2000, pp. 311-315
Citations number
19
Categorie Soggetti
Chemistry
Journal title
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG
ISSN journal
09411216 → ACNP
Volume
342
Issue
3
Year of publication
2000
Pages
311 - 315
Database
ISI
SICI code
0941-1216(2000)342:3<311:ASSOEP>2.0.ZU;2-#
Abstract
A new efficient method for the stereoselective preparation of trans-2,5-bis (alkyloxymethyl)pyrrolidines (7) using easily available starting materials is described. The main step of this synthesis is the stereoselective format ion of the pyrrolidine ring by the 1,3-dipolar cycloaddition reaction of an in situ generated azomethine ylide. Both enantiomers of the C-2-symmetric auxiliaries are prepared separately in a short reaction sequence.