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Phenanthrene derivatives
Q 1090 New Synthesis of Vaulted Biaryl Ligands via the Snieckus Phenol Synthesis. —
24- 094 In contrast to the method of Snieckus, naphthalene carboxamides (I) are subjected to
ortho-metalation in the absence of TMEDA. The base-induced intramolecular cycliza-
tions of amides (III) is successful with methyllithium and give high yields of the
phenanthrols (IV). Derivative (IVb) is converted to VAPOL ligand (V) via oxidative
dimerization at high temperature. The consequent deracemization in the presence of
(-)-sparteine affords the (S)-isomer in optically pure form. — (YU, S.;
RABALAKOS, C.; MITCHELL, W. D.; WULFF*, W. D.; Org. Lett. 7 (2005) 3,
367-369; Dep. Chem., Mich. State Univ., East Lansing, MI 48824, USA; Eng.) —
Steudel