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2005
Phenanthrene derivatives
Q 1090
New Synthesis of Vaulted Biaryl Ligands via the Snieckus Phenol Synthesis. —
contrast to the method of Snieckus, naphthalene carboxamides (I) are subjected to
24- 094 In
ortho-metalation in the absence of TMEDA. The base-induced intramolecular cyclizations 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.) —
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