Stereodivergent synthesis of enantioenriched azepino[3,4,5-<i>cd</i>]-indoles <i>via</i> cooperative Cu/Ir-catalyzed asymmetric allylic alkylation and intramolecular Friedel

Stereodivergent synthesis of enantioenriched azepino[3,4,5-cd]-indoles via cooperative Cu/Ir-catalyzed asymmetric allylic alkylation and intramolecular Friedel–Crafts reaction

Published:2022 Issue:17 Volume:13 Page:4801-4812
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Xiao Lu¹²,Li Bo³,Xiao Fan¹,Fu Cong¹,Wei Liang¹^ORCID,Dang Yanfeng³^ORCID,Dong Xiu-Qin¹^ORCID,Wang Chun-Jiang¹²^ORCID

Affiliation:

1. Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China

2. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China

3. Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University, Tianjin, 300072, China

Abstract

A stereodivergent synthesis of azepino[3,4,5-cd]-indoles bearing three stereogenic centers was established via synergistic dual-metal catalysis followed by acid-promoted epimerization, and up to all eight stereoisomers could be predictably achieved.

Funder

Natural Science Foundation of Hubei Province

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/SC/D1SC07271D

Reference117 articles.

1. Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery

2. A Planning Strategy for Diversity-Oriented Synthesis