An approach to new chiral bicyclic imines and amines via Horner-Wadsworth-Emmons reaction

Jakub Iwanejko; Mateusz Sowiński; Elżbieta Wojaczyńska; Tomasz K Olszewski; Marcin Górecki

doi:10.1039/d0ra02646h

An approach to new chiral bicyclic imines and amines via Horner-Wadsworth-Emmons reaction

RSC Adv. 2020 Apr 9;10(25):14618-14629. doi: 10.1039/d0ra02646h. eCollection 2020 Apr 8.

Authors

Jakub Iwanejko¹, Mateusz Sowiński¹, Elżbieta Wojaczyńska¹, Tomasz K Olszewski¹, Marcin Górecki²

Affiliations

¹ Faculty of Chemistry, Wrocław University of Science and Technology Wybrzeże Wyspiańskiego 27 50-370 Wrocław Poland elzbieta.wojaczynska@pwr.edu.pl tomasz.olszewski@pwr.edu.pl.
² Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka St 44/52 01-224 Warsaw Poland.

Abstract

New chiral bicyclic imines, enamines and amines were prepared via Horner-Wadsworth-Emmons reaction of hexahydroquinoxalin-2(1H)-one-derived phosphonate, as the source of a phosphonate carbanion, and a wide range of structurally diverse carbonyl substrates. The simplicity of the synthetic protocol, high selectivity, and broad substrate scope are the main advantages of the presented methodology.