Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source

Zheting Wang; Chunhui Yang; Jingchao Chen; Fan Yang; Ruhima Khan; Yong Yang; Xingfang Qiao; Zhimin Su; Baomin Fan

doi:10.1002/ajoc.202100201

Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source

Zheting Wang, Chunhui Yang, Jingchao Chen^*, Fan Yang, Ruhima Khan, Yong Yang, Xingfang Qiao, Zhimin Su, Baomin Fan^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

An efficient Pd/Zn co-catalyzed method for the asymmetric transfer hydrogenation of trifluoromethylated imines to chiral α-trifluoromethylated amines using methanol as the hydrogen source has been developed. The reaction showed good substrate scope and the products were obtained in excellent yields (up to 99%) with excellent enantioselectivity. The present methodology was compatible for the synthesis of deuterated chiral α-trifluoromethylated amines. On using CD₃OD as the deuterium source, deuterium incorporation up to 98% was observed without compromising the reaction outcome.

Original language	English
Pages (from-to)	1530-1535
Number of pages	6
Journal	Asian Journal of Organic Chemistry
Volume	10
Issue number	6
DOIs	https://doi.org/10.1002/ajoc.202100201
Publication status	Published - Jun 2021
Externally published	Yes

Keywords

Alcohols
Asymmetric transfer hydrogenation
Chiral α-trifluoromethylated amines
Deuteration
α-Trifluoromethylated imines

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10.1002/ajoc.202100201

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Wang, Z., Yang, C., Chen, J., Yang, F., Khan, R., Yang, Y., Qiao, X., Su, Z., & Fan, B. (2021). Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source. Asian Journal of Organic Chemistry, 10(6), 1530-1535. https://doi.org/10.1002/ajoc.202100201

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title = "Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source",

abstract = "An efficient Pd/Zn co-catalyzed method for the asymmetric transfer hydrogenation of trifluoromethylated imines to chiral α-trifluoromethylated amines using methanol as the hydrogen source has been developed. The reaction showed good substrate scope and the products were obtained in excellent yields (up to 99%) with excellent enantioselectivity. The present methodology was compatible for the synthesis of deuterated chiral α-trifluoromethylated amines. On using CD3OD as the deuterium source, deuterium incorporation up to 98% was observed without compromising the reaction outcome.",

keywords = "Alcohols, Asymmetric transfer hydrogenation, Chiral α-trifluoromethylated amines, Deuteration, α-Trifluoromethylated imines",

author = "Zheting Wang and Chunhui Yang and Jingchao Chen and Fan Yang and Ruhima Khan and Yong Yang and Xingfang Qiao and Zhimin Su and Baomin Fan",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = jun,

doi = "10.1002/ajoc.202100201",

language = "English",

volume = "10",

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AU - Wang, Zheting

AU - Yang, Chunhui

AU - Chen, Jingchao

AU - Yang, Fan

AU - Khan, Ruhima

AU - Yang, Yong

AU - Qiao, Xingfang

AU - Su, Zhimin

AU - Fan, Baomin

PY - 2021/6

Y1 - 2021/6

N2 - An efficient Pd/Zn co-catalyzed method for the asymmetric transfer hydrogenation of trifluoromethylated imines to chiral α-trifluoromethylated amines using methanol as the hydrogen source has been developed. The reaction showed good substrate scope and the products were obtained in excellent yields (up to 99%) with excellent enantioselectivity. The present methodology was compatible for the synthesis of deuterated chiral α-trifluoromethylated amines. On using CD3OD as the deuterium source, deuterium incorporation up to 98% was observed without compromising the reaction outcome.

AB - An efficient Pd/Zn co-catalyzed method for the asymmetric transfer hydrogenation of trifluoromethylated imines to chiral α-trifluoromethylated amines using methanol as the hydrogen source has been developed. The reaction showed good substrate scope and the products were obtained in excellent yields (up to 99%) with excellent enantioselectivity. The present methodology was compatible for the synthesis of deuterated chiral α-trifluoromethylated amines. On using CD3OD as the deuterium source, deuterium incorporation up to 98% was observed without compromising the reaction outcome.

KW - Alcohols

KW - Asymmetric transfer hydrogenation

KW - Chiral α-trifluoromethylated amines

KW - Deuteration

KW - α-Trifluoromethylated imines

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DO - 10.1002/ajoc.202100201

M3 - Article

AN - SCOPUS:85106005586

SN - 2193-5807

VL - 10

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JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 6

ER -

Asymmetric Transfer Hydrogenation of Trifluoromethylated Imines to Chiral α-Trifluoromethylated Amines With Alcohol as The Hydrogen Source

Abstract

Keywords

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