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Taming the Friedel–Crafts Reaction: Organocatalytic Approach to Optically Active 2,3‐Dihydrobenzofurans
Author(s) -
Albrecht Łukasz,
Ransborg Lars Krogager,
Lauridsen Vibeke,
Overgaard Mette,
Zweifel Theo,
Jørgensen Karl Anker
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105819
Subject(s) - optically active , stereocenter , friedel–crafts reaction , reactivity (psychology) , trimethylsilyl , chemistry , combinatorial chemistry , simple (philosophy) , organic chemistry , catalysis , enantioselective synthesis , pathology , medicine , philosophy , alternative medicine , epistemology
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.