Issue 43, 2009
From the journal:

Chemical Communications

Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane†

Wen-Bo Liu,a   Sheng-Cai Zheng,b   Hu He,a   Xiao-Ming Zhao,*b   Li-Xin Daia  and  Shu-Li You*a  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: slyou@mail.sioc.ac.cn
Fax: (+86) 21-54925087

b Department of Chemistry, Tongji University, 1239 Siping Lu, Shanghai 200092, China
E-mail: xmzhao08@mail.tongji.edu.cn

Abstract

Highly regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane (FBSM) has been realized by [Ir(COD)Cl]2/phosphoramidite, affording enantiopure fluorobis(phenylsulfonyl)methylated compounds bearing a terminal alkene, which could be converted to monofluoro-methylated ibuprofen in just two steps without loss of the optical purity (95% ee).

Graphical abstract: Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane

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Article information

DOI
https://doi.org/10.1039/B914315G
Article type
Communication
Submitted
16 Jul 2009
Accepted
02 Sep 2009
First published
15 Sep 2009

Chem. Commun., 2009, 6604-6606

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Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane

W. Liu, S. Zheng, H. He, X. Zhao, L. Dai and S. You, Chem. Commun., 2009, 6604 DOI: 10.1039/B914315G

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