The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand: A new route to anti-cyclopropylmethanol derivatives

Authors
Charette, AB Lebel, H Gagnon, A
Citation
Ab. Charette et al., The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand: A new route to anti-cyclopropylmethanol derivatives, TETRAHEDRON, 55(29), 1999, pp. 8845-8856
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
29
Year of publication
1999
Pages
8845 - 8856
Database
ISI
SICI code
0040-4020(19990716)55:29<8845:TSCOCA>2.0.ZU;2-7
Abstract
The diastereoselective cyclopropanation reaction of allylic alcohols in the presence of the chiral dioxaborolane ligand 1 was studied. Unprecedently h igh anti-selectivities were obtained with E-olefins when 2.2 equivalents of bis(iodomethyl)zinc and 1.1 equivalent of 1 were used. (C) 1999 Elsevier S cience Ltd. All rights reserved.