Stereoselective intramolecular radical addition of polyhaloacyl pendant groups to the 1,3-dihydro-2-imidazolone moiety: the chiral synthesis of threo-diaminocarboxylic acids

Citation
T. Katahira et al., Stereoselective intramolecular radical addition of polyhaloacyl pendant groups to the 1,3-dihydro-2-imidazolone moiety: the chiral synthesis of threo-diaminocarboxylic acids, TETRAHEDR L, 42(36), 2001, pp. 6319-6322
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
36
Year of publication
2001
Pages
6319 - 6322
Database
ISI
SICI code
0040-4039(20010903)42:36<6319:SIRAOP>2.0.ZU;2-F
Abstract
The intramolecular Ru(II)-catalyzed radical addition of trichloroacetyl and 2,2-dichloro-4-hexenoyl pendant groups to a 1,3-dihydro-2-imidazolone moie ty provides a perfectly stereocontrolled approach to the preparation of 1,2 -diamines which contain contiguous multi-stereocenters. Typical examples fo r this approach are given by the chiral synthesis of vicinal-diaminocarboxy lic acids, which are amino analogs of statine and MeBmt. (C) 2001 Elsevier Science Ltd. All rights reserved.