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Treatment of a range of homochiral unsaturated β-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with subsequent deprotection giving access to polyhydroxylated pyrrolidines. © 2009 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetasy.2009.02.014

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

07/05/2009

Volume

20

Pages

758 - 772