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Ring-closing iodoamination of (E)-configured, N-α-methyl-p- methoxybenzyl protected homoallylic amines upon treatment with I 2 and NaHCO 3 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. © 2012 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tet.2012.03.045

Type

Journal article

Journal

Tetrahedron

Publication Date

03/06/2012

Volume

68

Pages

4302 - 4319