Issue 23, 1993

Chemistry of Hantzsch cyclization: stereochemistry of the 2-hydroxy-1,2,3,4-tetrahydropyridine intermediate of Hantzsch cyclization. X-Ray molecular structure of diastereoisomers of 5-(2-cyanoethyl) 3-methyl 2-dimethoxymethyl-2-hydroxy-6-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydropyridine-3,5-dicarboxylates

Abstract

Hantzsch cyclization of cyanoethyl 3-aminocrotonate and (E,Z)-4,4-dialkoxy-2-benzylideneacetoacetates 12ah afforded the corresponding 3,4-trans-2-hydroxy-1,2,3,4-tetrahydropyridines 14ah with high stereoselectivity. 1H NMR and X-ray analyses of compound 14a established the configuration of 3-H and 4-H as trans and that of 3-H and 2-OH as trans also.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 3033-3039

Chemistry of Hantzsch cyclization: stereochemistry of the 2-hydroxy-1,2,3,4-tetrahydropyridine intermediate of Hantzsch cyclization. X-Ray molecular structure of diastereoisomers of 5-(2-cyanoethyl) 3-methyl 2-dimethoxymethyl-2-hydroxy-6-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydropyridine-3,5-dicarboxylates

T. Ogawa, K. Matsumoto, K. Hatayama, K. Kitamura and Y. Kita, J. Chem. Soc., Perkin Trans. 1, 1993, 3033 DOI: 10.1039/P19930003033

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