Reduction of the indole ring system: synthesis of 4, 5, 6, 7-tetrahydroindoles

CC McComas, DL Van Vranken

Index: McComas, Casey C.; Van Vranken, David L. Tetrahedron Letters, 1999 , vol. 40, # 46 p. 8039 - 8043

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Citation Number: 13

Abstract

A general two-step procedure for the reduction of indoles to the corresponding 4, 5, 6, 7- tetrahydroindoles has been developed. A regioselective Birch reduction followed by catalytic hydrogenation is employed to accomplish this transformation. Yields for the sensitive pyrrole products are typically between 40 and 50%. This method provides access to complex chiral pyrroles that cannot be readily prepared by other methods.