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Title 

Diastereoselective Iodoamidation of 3-Acetoxybut-1-enylamines: synthesis of 3-acetoxy-4-iodo-2-(p-methoxy-benzyl)pyrolidines

Authors 

Kyu Tae ChangKi Chang JangHo Yong ParkYoung Kook KimKi Hun ParkWoo Song Lee

Publisher 

Elsevier

Issue Date 

2001

Citation 

Heterocycles, vol. 55, no. 6, pp. 1173-1179

Keywords 

3 acetoxy 4 iodo 2 (4 methoxybenzyl)pyrrolidine derivativedrug synthesis

Abstract 

3α-Acetoxy-4α-iodo-2α-(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-trig cyclization and the diastereoselective addition of ethynylmagnesium bromide to aldehydes (9) by the chelation-controlled Cram cyclic model.

ISSN 

0385-5414

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2017-04-19


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