As part of a series of studies on synthesis of chiral 1-alkyltetrahydroisoquinolines, asymmetric synthesis of 1-alkoxycarbonylmethyl-l,2,3,4-tetrahydroisoquinoline (IV) was investigated. Two synthetic approaches using intermolecular and intramolecular Reformatsky-type reactions from (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline (1) were attempted, but high stereoselectivity could not be obtained. For the purpose of determining the absolute structures of the compounds (2, 3) obtained by the Reformatsky-type reactions, transformation of 3a to a chiral 1,3,4,6,7,11b-hexahvdro-2H-benzo[a]quinolizine (14) was investigated.
- Reformatsky reaction
- asymmetric synthesis
- diastereoselective alkylation
ASJC Scopus subject areas
- Drug Discovery