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Paper | Special issue | Vol 88, No. 2, 2014, pp.1163-1174
Published online, 1st August, 2013
DOI: 10.3987/COM-13-S(S)75
Enantioselective Synthesis of Tetrahydroquinoline Alkaloids (-)-Angustureine and (-)-Cuspareine from Chiral tert-Butanesulfinyl Imines

Juan A. Sirvent, Francisco Foubelo,* and Miguel Yus*

*Department of Organic Chemistry, Faculty of Sciences and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain

Abstract

The addition of a Grignard reagent to both enantiomeric N-tert-butanesulfinyl imines derived from 3-(2-bromophenyl)propanal 8 proceeded with high diastereoselectivity. The resulting sulfinamides 9 and 12 were easily transformed into tetrahydroquinoline alkaloids (-)-angustureine (4) and (-)-cuspareine (5) after three steps: N-desulfinylation, intramolecular N-arylation and N-methylation.