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

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 and involving a polarity reversal...

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Published inJournal of organic chemistry Vol. 85; no. 2; pp. 594 - 602
Main Authors Tan, Chang-Yin, Lu, Hong, Zhang, Jia-Lu, Liu, Jin-Yu, Xu, Peng-Fei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.01.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
CONSTRUCTION
PYRAZOLONES
SPIROCYCLIC OXINDOLES
3-COMPONENT
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Summary: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 and 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02684