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The Acetal Concept: Regioselective Access to ortho , ortho ‐Diphenols via Dibenzo‐1,3‐dioxepines
Author(s) -
Masters KyeSimeon,
Bräse Stefan
Publication year - 2013
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.201207485
Subject(s) - acetal , regioselectivity , chemistry , stereochemistry , computer science , hydrolysis , combinatorial chemistry , organic chemistry , catalysis
Traditional methods are ill‐suited for the synthesis of ortho , ortho ‐biphenols, a structural motif found in many polyphenolic natural products, as well as synthetically useful compounds such as the chiral ligands binol, vapol, and vanol. The new route consists of a radical‐based reaction of an acetal‐tethered biphenyl ether substrate and subsequent hydrolytic cleavage of the dibenzo‐1,3‐dioxepine intermediate.