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Note | Regular issue | Vol 55, No. 6, 2001, pp.1173-1179
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9206
Diastereoselective Iodoamidation of 3-Acetoxybut-1-enylamines: Synthesis of 3-Acetoxy-4-iodo-2-(p-methoxybenzyl)pyrrolidines

Kyu-Tae Chang, Ki Chang Jang, Ho-Yong Park, Young-Kook Kim, Ki Hun Park,* and Woo Song Lee*

*Department of Chemistry, Korea Advanced Institute of Science and Technology, 373-1, Kusung-Dong, Yusung-Gu, Taejon, 305-701, Korea

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.