Synthesis of 2,2-dialkylcyclopropylamines from β-chloroimines and application towards the synthesis of 1-amino-2,2-dialkylcyclopropane-carboxylic acids

Article abstract of DOI:10.1016/S0040-4020(01)86403-6

Base-induced 1,5-dehydrochlorination of β-chloroimines, having a relatively acidic hydrogen atom at carbon-1 of the N-substituent (e.g. benzyl, methoxycarbonylmethyl, α-methylbenzyl), afforded N-cyclopropylimines which were easily hydrolyzed into cyclopropylamines. This synthetic methodology was applied to the synthesis of the potentially plant growth regulating 1-amino-2,2-dialkylcyclopropanecarboxylic acids via oxidation with catalytic ruthenium(IV)oxide/sodium periodate of suitably N-protected 1-aryl-2,2-dialkylcyclopropylamines.