Ring-closing metathesis as a tool for the efficient preparation of chiral spirocyclic ethers from homoallylic alcohols

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Rosenberg S, Leino R
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Publication year: 2009
Journal: Tetrahedron Letters
Journal acronym: TETRAHEDRON LETT
Volume number: 50
Issue number: 38
Start page: 5305
End page: 5307
Number of pages: 3
ISSN: 0040-4039


Abstract

The preparation of chiral spirocyclic ethers via allylic etherification/olefin metathesis of homoallylic alcohols is investigated. This reaction sequence transforms the enantiopure substrate alcohols, synthesized by a one-pot asymmetric rhodium-catalyzed conjugate addition/metal-mediated allylation procedure, into the desired spite ethers with full conversions and in excellent isolated yields. The synthetic sequence provides an efficient means for a rapid construction of functionalized spiro ethers in a stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.


Keywords

Allylation, Asymmetric synthesis, Conjugate addition, Ring-closing metathesis, Spirocyclic ether

Last updated on 2019-21-09 at 03:58