Synlett 2017; 28(12): 1432-1436
DOI: 10.1055/s-0036-1588983
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© Georg Thieme Verlag Stuttgart · New York

Catalytic Synthesis of Chiral Phosphole Oxides via Desymmetric C–H Arylation of o-Bromoaryl Phosphine Oxides

Yan Lin
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. of China   eMail: ym_cui@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Wei-Yang Ma
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. of China   eMail: ym_cui@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Qiao-Ying Sun
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. of China   eMail: ym_cui@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Yu-Ming Cui*
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. of China   eMail: ym_cui@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Li-Wen Xu*
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. of China   eMail: ym_cui@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
› Institutsangaben

Gefördert durch: National Natural Science Foundation of China Grant / Award numbers ‘51303043’, ‘21472031’, ‘21503060’ Gefördert durch: Science and Technology Department of Zhejiang Province Grant / Award number ‘2015C31138’
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Publikationsverlauf

Received: 08. Februar 2017

Accepted after revision: 05. März 2017

Publikationsdatum:
11. April 2017 (online)


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Abstract

A palladium-catalyzed intramolecular direct arylation reaction of o-bromoaryl phosphine oxides was developed to afford a variety of P-stereogenic phosphole oxides in good yields. The enantioselectivities were closely associated with the specific structures of substrates, which ranged from 4–94%. As a result of ready availability of starting materials and simple operation to improve the enantioselectivities of the products with low ee values, the method provides a simple and straightforward procedure for the synthesis of P-stereogenic phosphole oxides.

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