Diastereoselective Bidirectional C(sp3)−H Bond Functionalization of Piperazine Compounds

Xiao Le Zhou; Chi Tung Yeung; Wesley Ting Kwok Chan; Ga Lai Law

doi:10.1002/adsc.202101187

Diastereoselective Bidirectional C(sp³)−H Bond Functionalization of Piperazine Compounds

Xiao Le Zhou, Chi Tung Yeung, Wesley Ting Kwok Chan, Ga Lai Law

Research output: Journal article publication › Journal article › Academic research › peer-review

Abstract

A highly diastereoselective bidirectional C(sp³)−H bond functionalization of piperazine compounds, triggered by a Lewis acid catalyzed sequential hydride shift/cyclization process, is reported. Catalysts and ligands are key factors that control the diastereoselectivity of the reaction. The reaction affords the product with good yield and high diastereoselectivity. Detailed investigation of the reaction mechanism reveals that the energy barrier between the cis products and trans products results in the diastereoselectivity of the reaction. The trans products, which have higher energy and which are generated from the cis products, act as intermediate products. (Figure presented.).

Original language	English
Pages (from-to)	732-737
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	4
DOIs	https://doi.org/10.1002/adsc.202101187
Publication status	Published - 15 Feb 2022

Keywords

bidirectional
C(sp)−H functionalization
Lewis acid catalysis
Sc(OTf)
trans/cis diastereoselectivity

ASJC Scopus subject areas

Catalysis
Organic Chemistry

More information

10.1002/adsc.202101187

http://hdl.handle.net/10397/94269

Cite this

@article{19642e2142f948c185d261dc79a7381c,

title = "Diastereoselective Bidirectional C(sp3)−H Bond Functionalization of Piperazine Compounds",

abstract = "A highly diastereoselective bidirectional C(sp3)−H bond functionalization of piperazine compounds, triggered by a Lewis acid catalyzed sequential hydride shift/cyclization process, is reported. Catalysts and ligands are key factors that control the diastereoselectivity of the reaction. The reaction affords the product with good yield and high diastereoselectivity. Detailed investigation of the reaction mechanism reveals that the energy barrier between the cis products and trans products results in the diastereoselectivity of the reaction. The trans products, which have higher energy and which are generated from the cis products, act as intermediate products. (Figure presented.).",

keywords = "bidirectional, C(sp)−H functionalization, Lewis acid catalysis, Sc(OTf), trans/cis diastereoselectivity",

author = "Zhou, {Xiao Le} and Yeung, {Chi Tung} and {Kwok Chan}, {Wesley Ting} and Law, {Ga Lai}",

note = "Funding Information: We are grateful for the financial support from National Natural Science Foundation of China, (NSFC,21875201) and Research Grants Council, University Grants Committee (15303020). We gratefully acknowledge the State Key Laboratory of Chemical Biology and Drug Discovery and The Hong Kong Polytechnic University [(a) University Research Facility in Chemical and Environmental Analysis (UCEA); (b) University Research Facility in Life Sciences (ULS)] for the resources. Publisher Copyright: {\textcopyright} 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.",

year = "2022",

month = feb,

day = "15",

doi = "10.1002/adsc.202101187",

language = "English",

volume = "364",

pages = "732--737",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "4",

}

TY - JOUR

T1 - Diastereoselective Bidirectional C(sp3)−H Bond Functionalization of Piperazine Compounds

AU - Zhou, Xiao Le

AU - Yeung, Chi Tung

AU - Kwok Chan, Wesley Ting

AU - Law, Ga Lai

N1 - Funding Information: We are grateful for the financial support from National Natural Science Foundation of China, (NSFC,21875201) and Research Grants Council, University Grants Committee (15303020). We gratefully acknowledge the State Key Laboratory of Chemical Biology and Drug Discovery and The Hong Kong Polytechnic University [(a) University Research Facility in Chemical and Environmental Analysis (UCEA); (b) University Research Facility in Life Sciences (ULS)] for the resources. Publisher Copyright: © 2022 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

PY - 2022/2/15

Y1 - 2022/2/15

N2 - A highly diastereoselective bidirectional C(sp3)−H bond functionalization of piperazine compounds, triggered by a Lewis acid catalyzed sequential hydride shift/cyclization process, is reported. Catalysts and ligands are key factors that control the diastereoselectivity of the reaction. The reaction affords the product with good yield and high diastereoselectivity. Detailed investigation of the reaction mechanism reveals that the energy barrier between the cis products and trans products results in the diastereoselectivity of the reaction. The trans products, which have higher energy and which are generated from the cis products, act as intermediate products. (Figure presented.).

AB - A highly diastereoselective bidirectional C(sp3)−H bond functionalization of piperazine compounds, triggered by a Lewis acid catalyzed sequential hydride shift/cyclization process, is reported. Catalysts and ligands are key factors that control the diastereoselectivity of the reaction. The reaction affords the product with good yield and high diastereoselectivity. Detailed investigation of the reaction mechanism reveals that the energy barrier between the cis products and trans products results in the diastereoselectivity of the reaction. The trans products, which have higher energy and which are generated from the cis products, act as intermediate products. (Figure presented.).

KW - bidirectional

KW - C(sp)−H functionalization

KW - Lewis acid catalysis

KW - Sc(OTf)

KW - trans/cis diastereoselectivity

UR - http://www.scopus.com/inward/record.url?scp=85122256942&partnerID=8YFLogxK

U2 - 10.1002/adsc.202101187

DO - 10.1002/adsc.202101187

M3 - Journal article

AN - SCOPUS:85122256942

SN - 1615-4150

VL - 364

SP - 732

EP - 737

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 4

ER -