S. Davies, James A. Lee, P. M. Roberts
Jun 3, 2012
Citations
0
Influential Citations
38
Citations
Journal
Tetrahedron
Abstract
Abstract 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.