Issue 44, 2005
From the journal:

Chemical Communications

Quinine/selectfluor combination induced asymmetric semipinacol rearrangement of allylic alcohols: an effective and enantioselective approach to α-quaternary β-fluoro aldehydes†

Min Wang,a   Bao Min Wang,a   Lei Shi,a   Yong Qiang Tu,*a   Chun-An Fan,a   Shao Hua Wang,a   Xiang Dong Hua  and  Shu Yu Zhanga  

* Corresponding authors

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

Abstract

A quinine/Selectfluor combination inducing rearrangement reaction of allylic alcohols was discovered, which involved a moderate yield with good enantioselective construction of α-quaternary carbon center and β-fluoro aldehyde under base condition.

Graphical abstract: Quinine/selectfluor combination induced asymmetric semipinacol rearrangement of allylic alcohols: an effective and enantioselective approach to α-quaternary β-fluoro aldehydes

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Article information

DOI
https://doi.org/10.1039/B510004F
Article type
Communication
Submitted
13 Jul 2005
Accepted
09 Sep 2005
First published
11 Oct 2005

Chem. Commun., 2005, 5580-5582

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Quinine/selectfluor combination induced asymmetric semipinacol rearrangement of allylic alcohols: an effective and enantioselective approach to α-quaternary β-fluoro aldehydes

M. Wang, B. M. Wang, L. Shi, Y. Q. Tu, C. Fan, S. H. Wang, X. D. Hu and S. Y. Zhang, Chem. Commun., 2005, 5580 DOI: 10.1039/B510004F

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