Synfacts 2006(4): 0348-0348  
DOI: 10.1055/s-2006-934334
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Tetrahydro-β-Carbolines and Via Pd-Catalyzed Intramolecular Allylic Alkylation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Bandini*, A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi*
Università di Bologna, Italy
Further Information

Publication History

Publication Date:
24 March 2006 (online)


1,2,3,4-Tetrahydro-β-carbolines (THBC) are an important class of indole-containing alkaloids with biological and medicinal importance. This report describes the use of a Pd-catalyzed asymmetric allylic alkylation (AAA, Trost reaction) to generate THBC derivatives as well as the syn­thesis of tetrahydro-γ-carbolines (THGCs). A ­thorough screening of ‘privileged’ P,P- and P,N-ligands was done and the optimum conditions employed Li2CO3 as the base. Indole substrates with electron-donating and electron-withdrawing groups were tested, with the former giving significantly higher enantiomeric excesses.