1376622-76-2Relevant academic research and scientific papers
Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: Application to the asymmetric synthesis of (-)-codonopsinine
Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.,West, Callum J.
, p. 4302 - 4319 (2012/07/16)
Ring-closing iodoamination of (E)-configured, N-α-methyl-p- methoxybenzyl protected homoallylic amines upon treatment with I2 and NaHCO3 in MeCN occurs with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr.
