A novel AlEt3-promoted tandem reductive rearrangement of 1-benzyloxy-2,3-epoxides: new route to 2-quaternary 1,3-diol units

De Run Li; Wu Jiong Xia; Yong Qiang Tu; Fu Min Zhang; Lei Shi

doi:10.1039/B209948A

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A novel AlEt₃-promoted tandem reductive rearrangement of 1-benzyloxy-2,3-epoxides: new route to 2-quaternary 1,3-diol units†

De Run Li,^a Wu Jiong Xia,^a Yong Qiang Tu,*^a Fu Min Zhang^a and Lei Shi^a

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* Corresponding authors

^a Department of Chemistry & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P. R. China
E-mail: tuyq@lzu.edu.cn
Fax: 86-931-8912582
Tel: 86-931-8912410

Abstract

A novel and highly stereoselective tandem rearrangement–reduction reaction of 1-benzyloxy-2,3-epoxide, under the promotion of triethylaluminum (AlEt₃), has been developed to construct a quaternary stereocenter and the hydroxymethyl attached to the carbon center in one-step.

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Experimental section DOC (284K)

Article information

DOI: https://doi.org/10.1039/B209948A
Article type: Communication
Submitted: 11 Oct 2002
Accepted: 08 Jan 2003
First published: 25 Feb 2003

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Chem. Commun., 2003, 798-799

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A novel AlEt₃-promoted tandem reductive rearrangement of 1-benzyloxy-2,3-epoxides: new route to 2-quaternary 1,3-diol units

D. R. Li, W. J. Xia, Y. Q. Tu, F. M. Zhang and L. Shi, Chem. Commun., 2003, 798 DOI: 10.1039/B209948A

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