Citation: Jia Xiaofei, Ren Xinyi, Wang Zheng, Xia Chungu, Ding Kuiling. Pyrrolyl-Based Phosphoramidite/Rh Catalyzed Asymmetric Hydroformylation of 1, 1-Disubstituted Olefins[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 207-214. doi: 10.6023/cjoc201809033 shu

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

Corresponding author: Xia Chungu, cgxia@lzb.ac.cn Ding Kuiling, kding@mail.sioc.ac.cn
Received Date: 26 September 2018
Revised Date: 10 October 2018
Available Online: 19 January 2018
Fund Project: the National Natural Science Foundation of China 21790333Project 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 Sciencesthe Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000the Key Research Program of Frontier Sciences QYZDY-SSW-SLH012

Figures(2)

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.
- hydroformylation,
- olefin,
- Rhodium,
- asymmetric catalysis,
- phosphoramidite
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