Issue 15, 2020
From the journal:

Chemical Science

A chiral cobalt(ii) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction†

Bin Shen, ORCID logo a   Qianwen He, ORCID logo a   Shunxi Dong, ORCID logo a   Xiaohua Liu ORCID logo *a  and  Xiaoming Feng ORCID logo *a  

* Corresponding authors

a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
E-mail: liuxh@scu.edu.cn, xmfeng@scu.edu.cn

Abstract

A chiral N,N′-dioxide/cobalt(II) complex catalyzed highly diastereoselective and enantioselective tandem aza-Piancatelli rearrangement/intramolecular Diels–Alder reaction has been disclosed. Various valuable hexahydro-2a,5-epoxycyclopenta[cd]isoindoles bearing six contiguous stereocenters have been obtained in good yields with excellent diastereo- and enantio-selectivities from a wide range of both readily available 2-furylcarbinols and N-(furan-2-ylmethyl)anilines.

Graphical abstract: A chiral cobalt(ii) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction

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Article information

DOI
https://doi.org/10.1039/D0SC00542H
Article type
Edge Article
Submitted
29 Jan 2020
Accepted
11 Mar 2020
First published
11 Mar 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 3862-3867

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A chiral cobalt(II) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction

B. Shen, Q. He, S. Dong, X. Liu and X. Feng, Chem. Sci., 2020, 11, 3862 DOI: 10.1039/D0SC00542H

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