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

Chem Commun (Camb)

Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan.

Published: December 2024

AI Article Synopsis

  • - P2-Bu, a phosphazene base, effectively catalyzes a three-component reaction that combines diethyl phosphite, cinnamonitrile derivatives, and -Boc imines to create β-aminophosphonates.
  • - This reaction is notable for producing compounds with a tetrasubstituted carbon while maintaining high levels of diastereoselectivity.
  • - It introduces a new approach for a rare reaction type called 1,1-difunctionalization of an electron-deficient alkene, expanding the methods available for reactions catalyzed by Brønsted bases.

Article Abstract

Phosphazene base, P2-Bu, efficiently catalyzed the telescopic three-component reaction of diethyl phosphite, cinnamonitrile derivatives, and -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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Source
http://dx.doi.org/10.1039/d4cc05169fDOI Listing

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