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

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Title
Diastereoselective Iodoamidation of 3-Acetoxybut-1-enylamines: synthesis of 3-acetoxy-4-iodo-2-(p-methoxy-benzyl)pyrolidines
Author(s)
Kyu Tae Chang; Ki Chang Jang; Ho Yong Park; Young Kook Kim; Ki Hun Park; Woo Song Lee
Bibliographic Citation
Heterocycles, vol. 55, no. 6, pp. 1173-1179
Publication Year
2001
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
Publisher
Elsevier
DOI
http://dx.doi.org/10.3987/com-01-9206
Type
Article
Appears in Collections:
Division of Biomaterials Research > Industrial Bio-materials Research Center > 1. Journal Articles
Jeonbuk Branch Institute > Functional Biomaterial Research Center > 1. Journal Articles
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