Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation
Jinguo Long, Rongrong Yu, Jihui Gao, Xianjie Fang
Abstract
Enantioselective auto-tandem catalysis represents a challenging yet highlight attractive topic in the field of asymmetric catalysis. In this context, we describe a dual catalytic cycle that merges allylic cyanation and asymmetric hydrocyanation. The one-pot conversion of a broad array of allylic alcohols into their corresponding 1,3-dinitriles proceeds in good yield with high enantioselectivity. The products are densely functionalized and can be easily transformed to chiral diamines, dinitriles, diesters, and piperidines. Mechanistic studies clearly support a novel sequential cyanation/hydrocyanation pathway.
Topics & Concepts
HydrocyanationCyanationEnantioselective synthesisAllylic rearrangementChemistryTandemContext (archaeology)Combinatorial chemistryCatalysisOrganic chemistryStereochemistryMaterials sciencePaleontologyComposite materialBiologyAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions