Tetrahedron

Applications of the thermal ene reaction of aldehyde t-butyl-and phenyl-hydrazones

JE Baldwin, RM Adlington, AU Jain, JN Kolhe…

Index: Baldwin, Jack E.; Adlington, Robert M.; Jain, Ashok U.; Kolhe, Jayant N.; Perry, Matthew W. D. Tetrahedron, 1986 , vol. 42, # 15 p. 4247 - 4252

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Citation Number: 33

Abstract

The Thermal Ene reaction of aldehyde t-butyl- and phenyl- hydrazones with enophiles gave C-trapped azo-adducts which can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, γ-alkyl-2-pyrrolidones, and γ-amino-esters. ... This reduction gave a mixture (ca. 1:1) of the hydrochloride salts of γ-amino-esters 17 and cyclohexylamine in high yield from the azo-esters 5 (R 2 -Ph). ... Zhang J.-H. , Wang M.-X. , Huang Z.-T.