Palladium-Catalyzed Stereospecific Coupling of BINOL-bistriflates and Zinc Cyanide and Applications in the Synthesis of 1,1′-Binaphthyl-2,2′-bisoxazolines (BOXAX)

Abstract

A palladium-catalyzed synthesis of enantiopure [1,1′-binaphthalene]-2,2′-dicarbonitriles from BINOL-bistriflates and zinc cyanide is reported. This cross-coupling reaction employs a 0.1–5 mol% catalyst loading, and is scalable and stereospecific. The synthetic applications of this reaction are demonstrated by product derivatizations and the synthesis of [1,1′-binaphthalene]-2,2′-bisoxazolines (BOXAX).

Key words

atropchiral compounds - palladium - cyanation - cross-coupling - stereospecific - chiral ligand

Publication History

Received: 10 May 2022

Accepted after revision: 05 July 2022

Accepted Manuscript online:
05 July 2022

Article published online:
28 July 2022

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