Studies in the stereoselective synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines

Abstract

Isoquinoline alkaloids and analogs play an important role in today's pharmaceutical industry. The need to synthesize single stereoisomers of these alkaloids is important. Many times only a single stereoisomer exhibits the desired activity, while other stereoisomers of the alkaloid exhibit undesired side effects. The stereoselective synthesis of 1, 1-disubstituted 1,2,3,4- tetrahydroisoquinolines using Reissert compound chemistry containing chiral acyl auxiliaries was studied with the ultimate goal of synthesizing spirobenzylisoquinoline alkaloids.