Author
Listed:
- Jia-Wang Wang
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Yan Li
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Wan Nie
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Zhe Chang
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Zi-An Yu
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Yi-Fan Zhao
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Xi Lu
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
- Yao Fu
(Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China)
Abstract
To increase the reliability and success rate of drug discovery, efforts have been made to increase the C(sp3) fraction and avoid flat molecules. sp3-Rich enantiopure amines are most frequently encountered as chiral auxiliaries, synthetic intermediates for pharmaceutical agents and bioactive natural products. Streamlined construction of chiral aliphatic amines has long been regarded as a paramount challenge. Mainstream approaches, including hydrogenation of enamines and imines, C–H amination, and alkylation of imines, were applied for the synthesis of chiral amines with circumscribed skeleton structures; typically, the chiral carbon centre was adjacent to an auxiliary aryl or ester group. Herein, we report a mild and general nickel-catalysed asymmetric reductive hydroalkylation to effectively convert enamides and enecarbamates into drug-like α-branched chiral amines and derivatives. This reaction involves the regio- and stereoselective hydrometallation of an enamide or enecarbamate to generate a catalytic amount of enantioenriched alkylnickel intermediate, followed by C–C bond formation via alkyl electrophiles.
Suggested Citation
Jia-Wang Wang & Yan Li & Wan Nie & Zhe Chang & Zi-An Yu & Yi-Fan Zhao & Xi Lu & Yao Fu, 2021.
"Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines,"
Nature Communications, Nature, vol. 12(1), pages 1-10, December.
Handle:
RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-21600-x
DOI: 10.1038/s41467-021-21600-x
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Citations
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Cited by:
- Xiao-Xu Wang & Yuan-Tai Xu & Zhi-Lin Zhang & Xi Lu & Yao Fu, 2022.
"NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes and the ligand effects on regioselectivity,"
Nature Communications, Nature, vol. 13(1), pages 1-10, December.
- Qian Gao & Wei-Cheng Xu & Xuan Nie & Kang-Jie Bian & Hong-Rui Yuan & Wen Zhang & Bing-Bing Wu & Xi-Sheng Wang, 2024.
"Regio‐ and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes,"
Nature Communications, Nature, vol. 15(1), pages 1-9, December.
- Yao Zhang & Deyong Qiao & Mei Duan & You Wang & Shaolin Zhu, 2022.
"Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates,"
Nature Communications, Nature, vol. 13(1), pages 1-8, December.
- Jiangtao Ren & Zheng Sun & Shuang Zhao & Jinyuan Huang & Yukun Wang & Cheng Zhang & Jinhai Huang & Chenhao Zhang & Ruipu Zhang & Zhihan Zhang & Xu Ji & Zhihui Shao, 2024.
"Enantioselective synthesis of chiral α,α-dialkyl indoles and related azoles by cobalt-catalyzed hydroalkylation and regioselectivity switch,"
Nature Communications, Nature, vol. 15(1), pages 1-14, December.
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