359865-08-0Relevant articles and documents
Diastereoselective iodoamidation of 3-acetoxybut-1-Enylamines: Synthesis of 3-acetoxy-4-iodo-2-(p-methoxybenzyl)pyrrolidines
Chang, Kyu-Tae,Jang, Ki Chang,Park, Ho-Yong,Kim, Young-Kook,Park, Ki Hun,Lee, Woo Song
, p. 1173 - 1179 (2007/10/03)
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.