Phosphazene base-catalyzed telescopic three-component reaction involving 1,1-difunctionalization of electron-deficient alkenes

Phosphazene base, P2-<i>t</i>Bu, efficiently catalyzed the telescopic three-component reaction of diethyl phosphite, cinnamonitrile derivatives, and <i>N</i>-Boc imines, providing β-aminophosphonates having a tetrasubstituted carbon in a highly diastereoselective manner. The reaction involves the little-known 1,1-difunctionalization of an electron-deficient alkene, offering a new format for the three-component reaction under Brønsted base catalysis.

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Publication Details

Journal
Chemical Communications
Published
2024-11-28
DOI
https://doi.org/10.1039/d4cc05169f
Citations
2
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
0.50

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article

Phosphazene base-catalyzed telescopic three-component reaction involving 1,1-difunctionalization of electron-deficient alkenes

Masahiro Terada, Sho Yamaguchi, Azusa Kondoh
2 citations
Chemical Communications
Multicomponent Synthesis of Heterocycles
0.50
article

Phosphazene base-catalyzed telescopic three-component reaction involving 1,1-difunctionalization of electron-deficient alkenes

Masahiro Terada, Sho Yamaguchi, Azusa Kondoh
article en
2 citations

Abstract

Phosphazene base, P2-<i>t</i>Bu, efficiently catalyzed the telescopic three-component reaction of diethyl phosphite, cinnamonitrile derivatives, and <i>N</i>-Boc imines, providing β-aminophosphonates having a tetrasubstituted carbon in a highly diastereoselective manner. The reaction involves the little-known 1,1-difunctionalization of an electron-deficient alkene, offering a new format for the three-component reaction under Brønsted base catalysis.

Chemical CommunicationsVol. 61(2)
Tohoku University (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 37%
Multicomponent Synthesis of Heterocycles
0.50
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