Palladium-Catalyzed Double Carbopalladation/syn-Insertion Cascade toward a Pragmatic Synthesis of Aminated Polyheterocyclic 1,2-Benzothiazepine 1-Oxides

Zhigang Huang; Longji Dai; Zhiyuan Chen

doi:10.1055/a-1975-4377

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(06): 989-999
DOI: 10.1055/a-1975-4377

paper

Palladium-Catalyzed Double Carbopalladation/syn-Insertion Cascade toward a Pragmatic Synthesis of Aminated Polyheterocyclic 1,2-Benzothiazepine 1-Oxides

Autor*innen

Zhigang Huang

^aCollege of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China
Longji Dai

^aCollege of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China
Zhiyuan Chen ∗

^aCollege of Chemistry & Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China

^bKey Laboratory of Novel Targets and Drug Study for Neural Repair of Zhejiang Province, School of Medicine, Zhejiang University City College, Hangzhou 310015, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

A palladium-catalyzed tandem cyclization reaction was developed, which offers a pragmatic synthesis of aminated tetracyclic 1,2-benzothiazepine 1-oxides bearing a highly fused medium-sized cyclic unit. An acetyl (Ac) group was found to be the optimal protecting group for sulfoximines to reduce the nucleophilic ability of the N atom, thus efficiently suppressing the formation of intramolecular 5-exo-dig cyclization side products. The transformation proceeds through a double syn-carbopalladation/annulation sequence to construct the rigid tetracyclic carbo-heterocyclic framework with excellent chemoselectivity and regioselectivity.

Key words

palladium catalysis - carbopalladation - cascade reaction - polyheterocycles - 1,2-benzothiazepine 1-oxides - sulfoximines

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Referenzen

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