Asymmetric Organocatalytic [4 + 1] Annulations Involving Polarity Reversal Process: A Tandem Catalytic Approach to Highly Functionalized Spiropyrazolone Derivatives.

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ID: 69952
2019
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Abstract
A tandem catalytic strategy for the asymmetric synthesis of spirocyclopentanone pyrazolones bearing three contiguous stereocenters and two quaternary carbons with good stereoselectivities has been developed. This strategy, using pyrazolones as efficient C1 synthons, involving a polarity reversal process, not only overcame the energy barrier of the dearomatization process, but also avoided nucleophilic addition of the hydroxy group in the enol form tautomer. Futhermore, spirocyclopentanones could be transformed into spirocyclohexamide pyrazolone with the lawesson reagent.
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Authors Tan, Chang-Yin;Lu, Hong;Zhang, Jia-Lu;Liu, Jin-Yu;Xu, Peng-Fei;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b02684
URL
Keywords
synthesis antipyrine pyrazolone schiffbase

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