Asymmetric Synthesis of Planar Chiral Carbonitriles and Amines via Carbene-Catalyzed Kinetic Resolution

Ya Lv; Chengli Mou; Qian Liu; Liangzhen Shu; Yuanlin Cai; Xiaokang Lv; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acs.orglett.3c04342

Asymmetric Synthesis of Planar Chiral Carbonitriles and Amines via Carbene-Catalyzed Kinetic Resolution

Ya Lv, Chengli Mou, Qian Liu, Liangzhen Shu, Yuanlin Cai, Xiaokang Lv, Zhichao Jin^*, Yonggui Robin Chi^*

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. The resulting optically pure planar chiral products hold significant potential for applications in asymmetric synthesis and antibacterial pesticide development.

Original language	English
Pages (from-to)	1584-1588
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.3c04342
Publication status	Published - Mar 1 2024
Externally published	Yes

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Publisher Copyright:
© 2024 American Chemical Society

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. The resulting optically pure planar chiral products hold significant potential for applications in asymmetric synthesis and antibacterial pesticide development.",

author = "Ya Lv and Chengli Mou and Qian Liu and Liangzhen Shu and Yuanlin Cai and Xiaokang Lv and Zhichao Jin and Chi, {Yonggui Robin}",

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doi = "10.1021/acs.orglett.3c04342",

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T1 - Asymmetric Synthesis of Planar Chiral Carbonitriles and Amines via Carbene-Catalyzed Kinetic Resolution

AU - Lv, Ya

AU - Mou, Chengli

AU - Liu, Qian

AU - Shu, Liangzhen

AU - Cai, Yuanlin

AU - Lv, Xiaokang

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2024/3/1

Y1 - 2024/3/1

N2 - We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. The resulting optically pure planar chiral products hold significant potential for applications in asymmetric synthesis and antibacterial pesticide development.

AB - We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. The resulting optically pure planar chiral products hold significant potential for applications in asymmetric synthesis and antibacterial pesticide development.

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U2 - 10.1021/acs.orglett.3c04342

DO - 10.1021/acs.orglett.3c04342

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SN - 1523-7060

VL - 26

SP - 1584

EP - 1588

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Asymmetric Synthesis of Planar Chiral Carbonitriles and Amines via Carbene-Catalyzed Kinetic Resolution

Abstract

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