Synthesis of spiroacetals using functionalised titanium carbenoids

Main, C.A., Rahman, S.S. and Hartley, R.C. (2008) Synthesis of spiroacetals using functionalised titanium carbenoids. Tetrahedron Letters, 49(32), pp. 4771-4774. (doi:10.1016/j.tetlet.2008.05.094)

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Abstract

Alkylidenation of lactones with functionalised titanium carbenoid reagents (Schrock carbenes) followed by acid-induced cyclisation of the resulting enol ethers constitutes a new method for the preparation of [4.4], [4.5] and [5.5] spiroacetals (1,6-dioxaspiro[4.4]nonanes, 1,6-dioxaspiro[4.5]decanes and 1,7-dioxaspiro[5.5]undecanes, respectively, sometimes termed 5,5-, 5,6- and 6,6-spiroketals). The titanium carbenoids are easily generated from readily available thioacetals.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Hartley, Professor Richard
Authors: Main, C.A., Rahman, S.S., and Hartley, R.C.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
Publisher:Elsevier
ISSN:0040-4039
Published Online:24 May 2008
Copyright Holders:Copyright © 2008 Elsevier
First Published:First published in Tetrahedron Letters 49(32):4771-4774
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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