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Pedrosa R, Andrés C, Rosón CD, et al. Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations. J Org Chem. 2003;68(5):1852-8doi: 10.1021/jo026525m.
Pedrosa, R., Andrés, C., Rosón, C. D., & Vicente, M. (2003). Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations. The Journal of organic chemistry, 68(5), 1852-8. https://doi.org/10.1021/jo026525m
Pedrosa, Rafael, et al. "Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations." The Journal of organic chemistry vol. 68,5 (2003): 1852-8. doi: https://doi.org/10.1021/jo026525m
Pedrosa R, Andrés C, Rosón CD, Vicente M. Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations. J Org Chem. 2003 Mar 07;68(5):1852-8. doi: 10.1021/jo026525m. PMID: 12608801.
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J Org Chem. 2003 Mar 07;68(5):1852-8. doi: 10.1021/jo026525m.

Temperature- and time-dependent stereochemical control in thermally induced keto-ene cyclizations.

The Journal of organic chemistry

Rafael Pedrosa, Celia Andrés, Carlos D Rosón, Martina Vicente

Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain. [email protected]

PMID: 12608801 DOI: 10.1021/jo026525m

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.

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