Tetrahydroisoquinolines. Part 2. Synthesis of 4-substituted N-methyl-1,2,3,4-tetrahydroisoquinolines via regio- and stereo-selective elaboration of tricarbonyl(N-methyl-1,2,3,4-tetrahydroisoqumoline)chromium
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2257-2261
- https://doi.org/10.1039/p19860002257
Abstract
Thermolysis of hexacarbonylchromium with N-methyltetrahydroisoquinoline generates the tricarbonyl-(N-methyltetrahydroisoquinoline)chromium complex (4). The 4-exo proton of complex (4) can be regio- and stereo-selectively removed with butyl-lithium and replaced stereoselectivity with retention of configuration by a variety of electrophiles [Mel, Etl, PhCH2Br, CD3OD, Cr(CO)3(PhF), MoOPH, Me2CO]. Oxidative decomplexation generates quantitatively the corresponding 4-methyl, ethyl, benzyl, deuterio, phenyl, hydroxy, and (1-hydroxy-1-methylethyl)-N-methyltetrahydroisoquinolines.This publication has 0 references indexed in Scilit: