Issue 40, 2021
From the journal:

New Journal of Chemistry

Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides†

Jie Huang, ORCID logo ‡abc   Shaofa Sun,‡b   Ping Ma,c   Jian Wang,bd   Kevin Lee, ORCID logo e   Yalan Xing, ORCID logo *e   Yang Wu*c  and  Gangqiang Wang*bf  

* Corresponding authors

a School of Pharmacy, Hubei University of Science and Technology, Xianning 437100, China

b Hubei Key Laboratory of Radiation Chemistry and Functional Materials, Non-power Nuclear Technology Collaborative Innovation Center, Hubei University of Science and Technology, Xianning 437100, China
E-mail: wgq20008@163.com

c Xianning Engineering Research Center for Healthy Environment, School of Basic Medical Sciences, Hubei University of Science and Technology, Xianning, China
E-mail: wysj2007@126.com

d School of Pharmaceutical Sciences, Tsinghua University, Beijing, China

e Department of Chemistry, William Paterson University of New Jersey, 300 Pompton Road, Wayne, New Jersey 07470, USA
E-mail: xingy@wpunj.edu

f School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China

Abstract

A highly diastereoselective spiro-cyclopropanation reaction of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides has been developed via base-induced annulation. This efficient and simple protocol features simple operations, mild conditions and excellent functional group compatibility. A variety of structurally interesting spiro-cyclopropanes were prepared in excellent yields and diastereomeric ratios (up to 97% yield and 20 : 1 dr). Also, ring expansion of the cyclopropanation product to quickly deliver a complex indeno[1,2-c]pyridazine structure showcased an interesting application of this method.

Graphical abstract: Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides

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Article information

DOI
https://doi.org/10.1039/D1NJ02886C
Article type
Paper
Submitted
12 Jun 2021
Accepted
10 Aug 2021
First published
23 Aug 2021

New J. Chem., 2021,45, 18776-18780

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Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides

J. Huang, S. Sun, P. Ma, J. Wang, K. Lee, Y. Xing, Y. Wu and G. Wang, New J. Chem., 2021, 45, 18776 DOI: 10.1039/D1NJ02886C

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