TETRAHYDROISOQUINOLINES .3. STEREOSELECTIVE SYNTHESIS OF CIS- AND TRANS-1,4-DISUBSTITUTED N-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINES AS THEIR TRICARBONYLCHROMIUM COMPLEXES

Autor: Julian Blagg, Stephen G. Davies, Alan Naylor, David Middlemiss, Steven J. Coote
Rok vydání: 2016
Předmět:
DOI: 10.1039/p19870000689
Popis: The 1-exo proton of tricarbonyl-4-exo-methyl- or tricarbonyl-4-exo-ethyl-2-methyl-1,2,3,4-tetrahydroisoquinolinechromium (6) and (7) can be regio- and stereo-selectively removed by t-butyl-lithium and replaced with a variety of electrophiles to give cis-1,4-disubstituted 2-methyl-1,2,3,4-tetrahydroisoquinoline complexes. Oxidative decomplexation generates the corresponding cis-1,4-disubstituted tetrahydroisoquinolines. Similar methodology applied to tricarbonyl (4-exo-trimethylsilyl-2-methyl-1,2,3,4-tetrahydroisoquinoline)chromium (15) gives, after desilylation, 1-exo-substituted tetrahydroisoquinoline complexes.
Databáze: OpenAIRE