Diastereoselective iodoamidation of 3-acetoxybut-1-enylamines: Synthesis of 3-acetoxy-4-iodo-2-(p-methoxybenzyl)pyrrolidines

Authors
Chang, KT Jang, KC Park, HY Kim, YK Park, KH Lee, WS
Citation
Kt. Chang et al., Diastereoselective iodoamidation of 3-acetoxybut-1-enylamines: Synthesis of 3-acetoxy-4-iodo-2-(p-methoxybenzyl)pyrrolidines, HETEROCYCLE, 55(6), 2001, pp. 1173-1179
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
6
Year of publication
2001
Pages
1173 - 1179
Database
ISI
SICI code
0385-5414(20010601)55:6<1173:DIO3SO>2.0.ZU;2-H
Abstract
3 alpha -Acetoxy-4 alpha -iodo-2 alpha-(p-methoxybenzyl)pyrrolidine (2) and its enanti-omer (3) were synthesized via diastereoselective iodoamidation, starting from D- or L-tyrosine. The key step contains unfavorable 5-endo-t rig cyclization and the diastereoselective addition of ethynylmagnesium bro mide to aldehydes (9) by the chelation-controlled Cram cyclic model.