Synthesis of E and Z Diastereoisomers of Benzyl Methyl-2-[3-(N-Substituted)indolyl] Cyclopropane-1,1-dicarboxylates and Their Stereoselective Reductive Cleavage

Abstract

A synthesis and separation procedure is described for the E and Z diastereoisomers of indolyl-cyclopropane dicarboxylates, IV and V, potential intermediates in the synthesis of the corresponding E and Z cyclopropyl analogs of the amino acid tryptophan and for other ring expansion reactions bearing the indole moiety. Also we have observed a stereoselective cleavage of the benzyl group of the E isomer, without affecting the cyclopropane ring.