New synthesis of vaulted biaryl ligands via the Snieckus phenol synthesis.

Su Yu, Constantinos Rabalakos, William D Mitchell, William D Wulff

Index: Org. Lett. 7 , 367, (2005)

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Abstract

[reaction: see text] In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route was examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus. The latter derivatives could be converted in a two-step sequence to 2-phenyl-4-phenanthrols in 60-72% overall yields. The utility of this method for the synthesis of VAPOL derivatives is demonstrated in the synthesis of (S)-7,7'-dimethyl-VAPOL.