Tetrahedron

Synthesis of E and Z 1-amino-2-aryl (alkyl)-cyclopropanecarboxylic acids via meldrum derivatives

ML Izquierdo, I Arenal, M Bernabe, EF Alvarez

Index: Izquierdo, M. L.; Arenal, I.; Bernabe, M.; Alvarez, E. Fernandez Tetrahedron, 1985 , vol. 41, # 1 p. 215 - 220

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Citation Number: 34

Abstract

The reaction of 5-arylidene (alkylidene)-2, 2-dimethyl-1, 3-dioxane-4, 6-diones (1)(Meldrum's acid derivatives) with dimethylsulfoxonium methylide gave 1-aryl (alkyl)-6, 6- dimethyl-4, 8-dioxo-5, 7-dioxaspiro [2.5] octanes (2) which, on treatment with sodium methoxide or ammonium hydroxide, gave exclusively E-1-methoxy-carboyl-2-aryl- cyclopropanecarboxylic acids (4) or Z-1-carbamoyl-2-aryl (alkyl)-cyclopropanecarboxylic ...

~67%

~80%

~58%

~41%

~26%

~25%

~70%

~19%

~80%

~55%

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