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A New Intramolecular Reaction for the Regioselective Debenzylation or Protection of Alcohols
Author(s) -
Madsen Jacob,
Bols Mikael
Publication year - 1998
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/(sici)1521-3773(19981204)37:22<3177::aid-anie3177>3.0.co;2-a
Subject(s) - intramolecular force , regioselectivity , chemistry , protecting group , reaction mechanism , combinatorial chemistry , reaction conditions , ionic bonding , group (periodic table) , medicinal chemistry , catalysis , organic chemistry , stereochemistry , ion , alkyl
Strained benzylidene acetals such as 1 can be prepared with a new intramolecular reaction that allows the selective removal of benzyl protecting groups neighboring free OH groups, without attacking other benzyl groups. The mechanism of this reaction, which is useful for carbohydrate synthesis, probably proceeds via ionic intermediates with neighboring group participation.