220850-36-2Relevant academic research and scientific papers
Chiral amino alcohols as intermediates in the stereocontrolled synthesis of 1,3-disubstituted tetrahydroisoquinolines and protoberberines
Carrillo,Badia,Dominguez,Anakabe,Osante,Tellitu,Vicario
, p. 1115 - 1120 (2007/10/03)
An efficient stereocontrolled synthetic approach to (3S)-3- aryltetrahydroisoquinoline 3d and (1S,3S)3-aryl-1- methyltetrahydroisoquinolines 3a-c by a Pictet-Spengler heterocyclization reaction of optically active (95% ee) (S)-1,2-diarylethylamines 2a-c is presented. An alternative route toward obtaining the epimeric derivative of 3a, tetrahydroisoquinoline (1R,3S)-6, was also achieved by a stereocontrolled ring opening process carried out on the oxazolotetrahydroisoquinoline 9. Tetrahydroisoquinoline 8 was employed for the stereoselective preparation of (5S,6S,14S)-6-phenyl-2,3,10,11-tetramethoxyprotoberberin-5-ol (12), a new type of 5,6-disubstituted protoberberine derivative with excellent (d.e>95% by 1H NMR) stereoselection.
