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Synlett 2018; 29(13): 1753-1758
DOI: 10.1055/s-0037-1610454
DOI: 10.1055/s-0037-1610454
letter
A Straightforward Access to Trifluoromethylated Spirobipyrazolines through a Double (3+2)-Cycloaddition of Fluorinated Nitrile Imines with Alkoxyallenes
The authors thank the National Science Center (NCN, Poland) for financial support in the framework of Preludium grant #2016/21/N/ST5/01254.Further Information
Publication History
Received: 24 April 2018
Accepted after revision: 29 May 2018
Publication Date:
02 July 2018 (online)
Dedicated to Professor Janusz Zakrzewski (University of Łódź) on the occasion of his 70th birthday
Abstract
Formal double (3+2)-cycloaddition of in situ generated trifluoroacetonitrile imines with alkoxyallenes proceeds in a highly regio- and diastereoselective manner to afford anti-configured spirobipyrazolines as the exclusive 2:1 adducts. Initial stepwise addition of the title electron-deficient 1,3-dipoles onto cumulenic reaction partner is postulated to explain the observed reaction pathway.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610454.
- Supporting Information
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References and Notes
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For selected examples of bioactive CF3-pyrazoles, see:
See also:
For synthetic methods towards trifluoromethylpyrazolines, see: