Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

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 alc...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-04, Vol.59 (17), p.6785-6789
Main Authors: Long, Jinguo, Yu, Rongrong, Gao, Jihui, Fang, Xianjie
Format: Article
Language:English
Subjects:
Alcohols
allylic alcohols
asymmetric hydrocyanation
Asymmetry
auto-tandem catalysis
Catalysis
chiral dinitriles
cyanation
Diamines
Diesters
Enantiomers
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Summary: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. All together now: A one‐pot conversion of allylic alcohols into 1,3‐dinitriles by enantioselective auto‐tandem catalysis has been developed. This novel asymmetric transformation, which consists of an allylic cyanation with concomitant hydrocyanation, proceeds in high yield and enantioselectivity for a broad range of substrates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202000704