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Synthesis 2021; 53(09): 1597-1604
DOI: 10.1055/s-0040-1705976
paper

An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

Qing-he Zhao
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
,
Guang-hao Yu
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
,
Ye-chen Meng
c   Hengshui No. 5 Middle School, Shengli West Road, Hengshui, Hebei Province, P. R. of China
,
Feng Sui
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
,
Mi-yi Yang
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
,
Li Liu
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
,
Hui-jie Li
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
,
Feng Li∗
b   College of Chemistry and Chemical Engineering, Shangqiu Normal University, 298 Wenhua Road, Shangqiu, Henan 476000, P. R. of China
,
Hai Ma∗
a   Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Bejing 100700, P. R. of China
› Author AffiliationsWe thank the Voluntary Program of China Academy of Chinese Medical Sciences (ZZ0908028) for financial support.
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Abstract

A series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane­ and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

Key words

styrylisoxazole - cyclization - trifluoromethyl - cyclopropane - inorganic base - phase-transfer catalyst

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705976.
  • Supporting Information


Publication History

Received: 02 October 2020

Accepted after revision: 21 October 2020

Article published online:
19 November 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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