Synthesis 2002(14): 2138-2142
DOI: 10.1055/s-2002-34391
PAPER
© Georg Thieme Verlag Stuttgart · New York

Controllable Monoaddition of Carbon Nucleophiles to 1,2,3,4-Diepoxybutane: Two-directional Chain Extension of a C2 Symmetric Four Carbon Diepoxide as a Route to Differentiated Syn 1,2-Diols

Robert K. Boeckman*, Xiaorong Liu
Department of Chemistry, University of Rochester, Rochester New York 14627-0216
Fax: +1(585)2754229; e-Mail: rkb@rkbmac.chem.rochester.edu;
Further Information

Publication History

Received 30 June 2002
Publication Date:
26 September 2002 (online)

Abstract

A strategy for the construction of unsymmetrically protected isolated syn 1,2-diols bearing various unsaturated appendages is described. Reaction conditions are described for selective monoaddition to C2 symmetric 1,2,3,4-diepoxybutane which permits both differential protection of the intermediate epoxy alcohols and a second chain elongation. This sequence provides access to unsymmetrical mono-protected diols bearing unsaturated appendages not readily accessible by asymmetric dihydroxylation.