Issue 18, 2021
From the journal:

Organic Chemistry Frontiers

Umpolung of donor–acceptor cyclopropanes via N-heterocyclic carbene organic catalysis†

Guihua Nie,‡a   Xuan Huang,‡b   Zhongyao Wang,‡a   Dingwu Pan,a   Junmin Zhang ORCID logo b  and  Yonggui Robin Chi ORCID logo *ac  

* Corresponding authors

a Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
E-mail: robinchi@ntu.edu.sg

b International Joint Research Center for Molecular Science, College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518060, China

c Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

Abstract

A carbene-catalyzed formal umpolung of donor–acceptor (D–A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D–A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities.

Graphical abstract: Umpolung of donor–acceptor cyclopropanes via N-heterocyclic carbene organic catalysis

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Article information

DOI
https://doi.org/10.1039/D1QO00826A
Article type
Research Article
Submitted
31 May 2021
Accepted
03 Jul 2021
First published
06 Jul 2021

Org. Chem. Front., 2021,8, 5105-5111

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Umpolung of donor–acceptor cyclopropanes via N-heterocyclic carbene organic catalysis

G. Nie, X. Huang, Z. Wang, D. Pan, J. Zhang and Y. R. Chi, Org. Chem. Front., 2021, 8, 5105 DOI: 10.1039/D1QO00826A

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