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

Organic & Biomolecular Chemistry Pub Date: 2019-04-11 DOI: 10.1039/C9OB00706G

Abstract

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.

Graphical abstract: Friedel–Crafts alkylation with α-bromoarylacetates for the preparation of enantioenriched 2,2-diarylethanols
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