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Synlett 1996; 1996(1): 85-86
DOI: 10.1055/s-1996-5336
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Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]: A Notable Catalyst for Enantiotopically Selective Aromatic Substitution Reactions of α-Diazocarbonyl Compounds

Nobuhide Watanabe, Takanori Ogawa, Yoshihito Ohtake, Shiro Ikegami, Shun-ichi Hashimoto*
  • *Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan
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Publication History

Publication Date:
31 December 2000 (online)

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Dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] catalyzes aromatic substitution reactions of 3-alkyl-substituted 1-diazo-3,3-diphenyl-2-propanones to give (S)-1-alkyl-2-phenyl-2-indanones featured by a chiral quaternary carbon atom in up to 98% ee, the effectiveness of which has been demonstrated by the first enantioselective synthesis of FR115427 [(S)-(+)-1-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride], a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist.

dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] - α-diazocarbonyl compounds - 1,1-disubstituted 2-indanones - chiral quaternary carbon atom - NMDA receptor antagonist