Taming the Friedel-Crafts reaction: organocatalytic approach to optically active 2,3-dihydrobenzofurans

Łukasz Albrecht; Lars Krogager Ransborg; Vibeke Lauridsen; Mette Overgaard; Theo Zweifel; Karl Anker Jørgensen

doi:10.1002/anie.201105819

Taming the Friedel-Crafts reaction: organocatalytic approach to optically active 2,3-dihydrobenzofurans

Angew Chem Int Ed Engl. 2011 Dec 23;50(52):12496-500. doi: 10.1002/anie.201105819. Epub 2011 Nov 7.

Authors

Łukasz Albrecht¹, Lars Krogager Ransborg, Vibeke Lauridsen, Mette Overgaard, Theo Zweifel, Karl Anker Jørgensen

Affiliation

¹ Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark.

PMID: 22065613
DOI: 10.1002/anie.201105819

Abstract

Fine-tuning: Three types of optically active trans-2,3-disubstituted-2,3-dihydrobenzofurans having three contiguous stereogenic centers can be efficiently accessed by one-pot reaction cascades (see scheme; TMS = trimethylsilyl). High substitution diversity of the final products can be achieved from the same common precursors by fine-tuning of their reactivity through simple structural modifications.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzofurans / chemical synthesis*
Benzofurans / chemistry
Catalysis
Molecular Structure
Stereoisomerism

Substances

Benzofurans
coumaran