HIGH-PRESSURE ORGANIC-CHEMISTRY .10. NOVEL NEUTRAL ALKYLATIONS OF INDOLES AND PYRROLES WITH VINYL EPOXIDES AT HIGH-PRESSURE

In organic synthesis, the most important reaction is alkylation. Alkylation reactions are generally catalyzed by either acid or base, but obviously, the mildest way to perform these reactions is to conduct them under neutral conditions. The high-pressure technique as one of these approaches has seen increased use in recent years.2 As a part of our program to develop new synthetic methods in this field,3 it has become of interest to investigate the alkylation of indoles or pyrroles. In this paper we describe an essentially noncatalyzed carbon-carbon bond formation of indoles and pyrroles with vinyl epoxides. The procedure constitutes a useful method to produce tryptophol derivatives, which are of interest as synthetic intermediates toward antibiotics such as indolmycin. © 1990, American Chemical Society. All rights reserved.