STEREOSELECTIVE SYNTHESIS OF CIS-2 AND TRANS-2-(INDOL-3-YL) CYCLOPROPYL AMINES, CARBOXYLIC-ACIDS, AND ESTERS

We report a general route for the synthesis of E and Z isomers of indo l-3-yl cyclopropyl amines, carboylic acids, and esters. These cyclopro pane containing molecules are of interest as conformationally constrai ned analogues of tryptamine and indole propionic acid, biologically ac tive indoles. The route involves reaction of vinyl indole with ethyl d iazoacetate, chromatographic separation of the E and Z stereoisomers o f the resulting cyclopropane esters, hydrolysis to form the E and Z cy clopropane acids, and formation of amines by the Curtius reaction.