A versatile method for the facile synthesis of enantiopure trans- and cis-2,5-disubstituted pyrrolidines

Authors
Wang, Q Sasaki, NA Riche, C Potier, P
Citation
Q. Wang et al., A versatile method for the facile synthesis of enantiopure trans- and cis-2,5-disubstituted pyrrolidines, J ORG CHEM, 64(23), 1999, pp. 8602-8607
Citations number
79
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
23
Year of publication
1999
Pages
8602 - 8607
Database
ISI
SICI code
0022-3263(19991112)64:23<8602:AVMFTF>2.0.ZU;2-9
Abstract
Treatment of(2S)-1-O-benzylglycerol-2,3-bistrifiate (2) with the trilithiat ed species of chiral building blocks 5-7 provided 2,3,5-trisubstituted pyrr olidines that were subjected to reductive desulfonylation to give trans-2,5 -disubstituted pyrrolidines 11-13, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the cia isomer 19. This two-step synthetic mehodology can furnish any one of the four possibl e diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60-72% ove rall yields.