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Nucleophilic Opening of Oxabicyclic Ring Systems
Author(s) -
Schindler Corinna S.,
Diethelm Stefan,
Carreira Erick M.
Publication year - 2009
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.200902046
Subject(s) - nucleophile , ring (chemistry) , scope (computer science) , substrate (aquarium) , chemistry , lewis acids and bases , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , computer science , programming language , catalysis , biology , ecology
With remarkable ease , even saturated [2.2.1]oxabicyclic systems of type 1 underwent Lewis acid mediated nucleophilic ring opening to provide rapid access to densely functionalized perhydroindoles ( n =1) and perhydroquinolines ( n =2, see scheme). Both amines and amides are suitable nucleophiles for this efficient transformation with broad substrate scope.