Dinuclear zinc-catalyzed asymmetric Friedel-Crafts alkylation/cyclization of 3-aminophenols with α,α-dicyanoolefins

An enantioselective Friedel-Crafts alkylation/cyclization tandem reaction of 3-aminophenols with α,α-dicyanoolefins has been performed successfully using a chiral dinuclear zinc catalyst, leading to a range of chiral 2-amino-4 H -chromenes (up to 98% yield and >99% ee). To the best of our knowled...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-09, Vol.57 (77), p.9854-9857
Main Authors: Yan, Hang, Jia, Shi-Kun, Geng, Yu-Huan, Han, Jiao-Jiao, Hua, Yuan-Zhao, Wang, Min-Can
Format: Article
Language:English
Subjects:
Alkylation
Aminophenol
Asymmetry
Cascade chemical reactions
Enantiomers
Friedel-Crafts reaction
Zinc
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An enantioselective Friedel-Crafts alkylation/cyclization tandem reaction of 3-aminophenols with α,α-dicyanoolefins has been performed successfully using a chiral dinuclear zinc catalyst, leading to a range of chiral 2-amino-4 H -chromenes (up to 98% yield and >99% ee). To the best of our knowledge, this is the first asymmetric example of the dinuclear zinc-catalysed functionalization of aromatic C(sp 2 )-H bonds. This is the first asymmetric example of the dinuclear zinc-catalysed functionalization of aromatic C(sp 2 )-H bonds.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc04177k