Synthesis of highly substituted cyclohexenes via mixed Lewis acid-catalyzed Diels-Alder reactions of highly substituted dienes and dienophiles.
[reaction: see text] A high-yielding method is described for the rapid synthesis of very hindered cyclohexenes by the Diels-Alder reaction of hindered silyloxy dienes and dienophiles using the mixed Lewis acid catalyst system (AlBr(3)/AlMe(3)). Thus, reaction of the hindered diene 4 with various substituted enones gave good yields of the expected cycloadducts even though both partners are quite sterically hindered.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
Ho
David
D
Chu
Hiufung V
HV
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes; D015394:Molecular Structure
D000475:Alkenes; D003510:Cyclohexanes; D053138:Cyclohexenes; C052568:cyclohexene