Preliminary Studies on the Stereochemistry of Emetine. I. Mercuric Acetate Dehydrogenation of (-)-2'-Acylemetines
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In this paper, it was shown that 1-alkyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives are dehydrogenated with the same reagent to afford 3-4-dihydro compounds, but the corresponding 2-acyl compounds resisted similar dehydrogenation.Abstract:
Mercuric acetate dehydrogenation of (-)-2'-acylemetines, which have the same configuration as (-)-emetine, was found to afford 5, 11b-dehydro-2'-acylemetines. In preliminary experiments, it was shown that 1-alkyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives are dehydrogenated with the same reagent to afford 3, 4-dihydro compounds, but the corresponding 2-acyl compounds resisted similar dehydrogenation. These results seem to strongly support Openshaw's view about the structure of tetradehydroemetine.read more
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Reduction asymetrique catalysee par des complexes de metaux de transition IV. synthese d'amines chirales au moyen d'un complexe de rhodium et d'isopropylidene dihydroxy-2,3 bis(diphenylphosphino)-1,4 butane (diop)
TL;DR: In this paper, a chiral rhodium complex with (+)-diop as ligand is used as a catalyst in asymmetric synthesis leading to amines and N -acyl derivatives.
Journal ArticleDOI
Alkylation of the isoquinoline skeleton in the 1-position
TL;DR: In this article, the nucleophilic reactivity in the l position of 1,2,3,4-tetrahydroisoquinoline is generated by lithiation of the N-pivaloyl- and N-phosphinoyl -derivatives.
Journal ArticleDOI
2-Bis (dimethylamino)phosphinoyl-1-lithio-1, 2, 3, 4-tetrahydroisoquinoline. A highly nucleophilic d1-reagent for the preparation of 1-substituted tetrahydroisoquinolines
Dieter Seebach,Masaaki Yoshifuji +1 more
TL;DR: In this article, the title compound was generated from the phosphoric amide 5 in tetrahydrofuran with butyllithium, which is stable at room temperature; its reactions with electrophiles furnish the products.