Friedel-Crafts alkylation with α-bromoarylacetates for the preparation of enantioenriched 2,2-diarylethanols

Highly enantioenriched 2,2-diarylethanols can be efficiently synthesized through the Friedel-Crafts alkylation of (hetero)arenes with configurationally labile α-bromoarylacetates. The substitution of highly diastereoenriched α-bromoarylacetates occurs in the presence of AgOTf, and the subsequent red...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-05, Vol.17 (18), p.4554-4563
Main Authors: Kim, Yongtae, Choi, Yun Soo, Hong, Su Kyung, Park, Yong Sun
Format: Article
Language:English
Subjects:
Alkylation
Aromatic compounds
Friedel-Crafts reaction
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:Highly enantioenriched 2,2-diarylethanols can be efficiently synthesized through the Friedel-Crafts alkylation of (hetero)arenes with configurationally labile α-bromoarylacetates. The substitution of highly diastereoenriched α-bromoarylacetates occurs in the presence of AgOTf, and the subsequent reduction affords diverse 2,2-diarylethanols with high yields and enantioselectivities up to 99 : 1 er. In addition, the application of this asymmetric synthetic methodology to the preparation of highly enantioenriched dihydrobenzofuran and indoline derivatives is demonstrated.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob00706g