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Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations
Rafael Pedrosa1, Celia Andrés, Carlos D Rosón
1Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain. pedrosa@qo.uva.es
The Journal of Organic Chemistry
|March 1, 2003
Abstract:
Reaction conditions determine the stereoselection in the intramolecular keto-ene reaction. The thermolysis of chiral 2-acyl-3-allyl-substituted 1,3-perhydrobenzoxazines derived from (-)-8-aminomenthol gives a mixture of only two cis-3-hydroxy-3,4-disubstituted pyrrolidine nuclei. The stereochemistry of the major diastereoisomer depends on both the temperature and the reaction time.