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Synthesis
DOI: 10.1055/a-2335-8566
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Special Topic Dedicated to Prof. H. Ila

Ring-Opening of Donor-Acceptor Cyclopropane Diester for the Synthesis of Oxime Esters and 2,3-Dihydroazete Ester

Neeraj Yadav
a   Lab No. 406, Department of Chemistry, Indian Institute ofTechnology Ropar, Rupnagar, Punjab 140001, India
,
Kritika Verma
a   Lab No. 406, Department of Chemistry, Indian Institute ofTechnology Ropar, Rupnagar, Punjab 140001, India
,
Arnab Das
b   Department of Chemistry, Indian Institute of Technology Mandi, Mandi, Himachal Pradesh 175005, India
,
Navpreet Kaur
a   Lab No. 406, Department of Chemistry, Indian Institute ofTechnology Ropar, Rupnagar, Punjab 140001, India
,
Prabal Banerjee  ∗
a   Lab No. 406, Department of Chemistry, Indian Institute ofTechnology Ropar, Rupnagar, Punjab 140001, India
› Author AffiliationsWe gratefully acknowledge the financial support from the Department of Science & Technology, India (DST, CRG/2022/006407) and the Council of Scientific & Industrial Research, India (CSIR).
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Abstract

A simple and efficient approach for the synthesis of privileged oxime esters by employing donor-acceptor cyclopropane diesters (DACs) as one of the potential precursors is reported. The strategy involves Lewis acid catalyzed ring-opening of DACs, resulting in an open-chain intermediate followed by the base-mediated construction of the corresponding oxime esters in a one-pot reaction. Moreover, the process also features the synthesis of diethyl 4-(4-methoxyphenyl)azete-2,2(3H)-dicarboxylate.

Key words

donor-acceptor cyclopropanes - zwitterionic compound - oxime esters - one-pot synthesis - bioactive compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2335-8566.
  • Supporting Information


Publication History

Received: 24 April 2024

Accepted after revision: 29 May 2024

Accepted Manuscript online:
29 May 2024

Article published online:
18 June 2024

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