Nickel-Catalyzed Asymmetric Hydrogenation for Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines

被引：18

作者：

Zhao, Yang ^{[1
,2
]}

Ding, Yi-Xuan ^{[1
]}

Wu, Bo ^{[1
]}

Zhou, Yong-Gui ^{[1
,3
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 15期

基金：

中国国家自然科学基金;

关键词：

RACEMIC ALLYLIC ALCOHOLS; ENANTIOSELECTIVE HYDROGENATION; REDUCTIVE AMINATION; OPTICAL RESOLUTION; CENTRAL CHIRALITY; PRACTICAL ACCESS; AMINO-ACID; PLANAR; PALLADIUM; EFFICIENT;

D O I：

10.1021/acs.joc.1c01011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel-catalyzed asymmetric hydrogenation for kinetic resolution of [2.2]paracyclophane-derived cyclic N-sulfonylimines was successfully developed. High selectivity factors were observed in most cases (s up to 89), providing the recovered materials and hydrogenation products in good yields with high levels of enantiopurity. The recovered materials and hydrogenation products are useful synthetic intermediates for the synthesis of planar chiral [2.2]paracyclophane-based compounds.

引用

页码：10788 / 10798

页数：11

共 8 条

[1] Kinetic Resolution of [2.2]Paracyclophane-Derived Cyclic N-Sulfonylimines via Palladium-Catalyzed Addition of Arylboronic Acids
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[2] Dearomatization of [2.2]Paracyclophane-Derived N-Sulfonylimines through Cyclopropanation with Sulfur Ylides
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[3] Nickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines
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[4] Efficient and Scalable Kinetic Resolution of Racemic 4-Formyl-[2.2]paracyclophane via Asymmetric Transfer Hydrogenation
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[7] Manganese-Catalyzed Asymmetric Hydrogenation for Atroposelective Dynamic Kinetic Resolution of Heterobiaryl Ketone N-Oxides
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[8] Low-Temperature Nickel-Catalyzed C-N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand
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