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Tandem Brønsted Acid Promoted and Nazarov Carbocyclizations of Enyne Acetals to Hydroazulenones
Author(s) -
Escalante Luz,
GonzálezRodríguez Carlos,
Varela Jesús A.,
Saá Carlos
Publication year - 2012
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.201205823
Subject(s) - enyne , tandem , brønsted–lowry acid–base theory , chemistry , ring (chemistry) , stereospecificity , combinatorial chemistry , stereochemistry , computer science , organic chemistry , catalysis , materials science , composite material
Ring the changes : Enyne acetals were easily converted into hydroazulene skeletons by a new and efficient metal‐free route involving a Brønsted acid promoted carbocyclization and a subsequent stereospecific Nazarov cyclization (see scheme). The versatility of this transformation also allowed assembly of interesting heteroaromatic tricyclic systems.