Pyrrolyl-Based Phosphoramidite/Rh Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Olefins

doi:10.6023/cjoc201809033

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 207-214.DOI: 10.6023/cjoc201809033 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

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手性吡咯亚磷酰胺/Rh催化的1,1-双取代烯烃的不对称氢甲酰化反应

贾肖飞^a,b, 任新意^a,b, 王正^a, 夏春谷^b, 丁奎岭^a

a 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032;
b 中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室兰州 730000

收稿日期:2018-09-26 修回日期:2018-10-10 发布日期:2018-10-20
通讯作者: 夏春谷, 丁奎岭 E-mail:kding@mail.sioc.ac.cn;cgxia@lzb.ac.cn
基金资助:
国家自然科学基金（No.21790333）、中国科学院前沿科学重点研究计划（No.QYZDY-SSW-SLH012）和中国科学院战略性先导科技专项（B类）（No.XDB20000000）资助项目.

Pyrrolyl-Based Phosphoramidite/Rh Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Olefins

Jia Xiaofei^a,b, Ren Xinyi^a,b, Wang Zheng^a, Xia Chungu^b, Ding Kuiling^a

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
b State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000

Received:2018-09-26 Revised:2018-10-10 Published:2018-10-20
Contact: 10.6023/cjoc201808048 E-mail:kding@mail.sioc.ac.cn;cgxia@lzb.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21790333), and the Key Research Program of Frontier Sciences (No. QYZDY-SSW-SLH012) & the Strategic Priority Research Program (No. XDB20000000) of the Chinese Academy of Sciences.

1. Pyrrolyl-Based Phosphoramidite/Rh Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Olefins.PDF(1598KB)

Abstract

A readily prepared chiral pyrrolylphosphinite has been found highly efficient for Rh(I) catalyzed asymmetric hydroformylation of 1,1-disubstituted olefins. Chiral linear aldehydes have been synthesized with high productivity (turnover number (TON) up to 8900), excellent regioselectivity, and good to high chemo- and enantio-selectivites (71%～86% ee). The reaction features ready catalyst preparation and wide functional group tolerance, thus will be of practical value in the use of asymmetric hydroformylation (AHF) for the synthesis of chiral α-alkyl-β-formylpropanoate analogues.

Key words: hydroformylation, olefin, Rhodium, asymmetric catalysis, phosphoramidite

Cite this article

Jia Xiaofei, Ren Xinyi, Wang Zheng, Xia Chungu, Ding Kuiling. Pyrrolyl-Based Phosphoramidite/Rh Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Olefins[J]. Chin. J. Org. Chem., 2019, 39(1): 207-214.

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手性吡咯亚磷酰胺/Rh催化的1,1-双取代烯烃的不对称氢甲酰化反应

Pyrrolyl-Based Phosphoramidite/Rh Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Olefins

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