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Stereoselectivity of the Diels—Alder Cycloadditions, Sodium Borohydride Reduction and 1,3-Dipolar Cycloadditions to Furan Derivatives

Ľ. Fišera, J. Melnikov, N. Prónayová, and P. Ertl

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, SK-812 31 Bratislava

 

Abstract: N-Phenyl- and N-(3,5-dichlorophenyl)maleimide react smoothly with furan to give endo and exo adducts depending on the reaction temperature. Semiempirical quantum-mechanical methods AM1 were used to rationalize this formation of adducts. The reduction of exo Diels-Alder adducts with sodium borohydride proceeds stereoselectively to yield the exo or endo hydroxylactams depending on the reaction temperature. 1,5-Dipolar cycloaddition of arylnitrile oxides to exo Diels-Alder adducts led exclusively to exo-exo cycloadducts.

Full paper in Portable Document Format: 494a186.pdf

 

Chemical Papers 49 (4) 186–191 (1995)

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