Protecting-group-free enantioselective tandem allylic substitution of o-phenylenediamines and o-aminophenols

Xuehua Kang; Chao Qian; He Yang; Jicheng Shi; Jerome Claverie; Wenjun Tang

Green Synthesis and Catalysis (May 2022)

Protecting-group-free enantioselective tandem allylic substitution of o-phenylenediamines and o-aminophenols

Xuehua Kang,
Chao Qian,
He Yang,
Jicheng Shi,
Jerome Claverie,
Wenjun Tang

Affiliations

Xuehua Kang: School of Physical Science and Technology, Shanghai Tech University, Shanghai 200031, China
Chao Qian: State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
He Yang: State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Jicheng Shi: College of Chemistry, Maoming Technology Center of Organic Materials, Guangdong University of Petrochemical Technology, Maoming 525000, China; Corresponding authors.
Jerome Claverie: Department of Chemistry, University of Sherbrooke, Sherbrooke J1K2R1, Canada; Corresponding authors.
Wenjun Tang: School of Physical Science and Technology, Shanghai Tech University, Shanghai 200031, China; State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China; School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China; Corresponding author. School of Physical Science and Technology, Shanghai Tech University, Shanghai 200031, China.

Journal volume & issue: Vol. 3, no. 2
pp. 185 – 189

Abstract

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A protecting-group-free enantioselective tandem allylic substitution of o-phenylenediamines and o-aminophenols is realized for the first time with a Pd-WingPhos catalyst, providing expedient access to a series of chiral vinyl-substituted heterocycles in excellent ee and yields under mild reaction conditions. The protocol is applied successfully to the synthesis of a cholesteryl ester transfer protein (CETP) inhibitor.

Published in Green Synthesis and Catalysis

ISSN: 2666-5549 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-synthesis-and-catalysis/

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