Synthesis, resolution, and determination of absolute configuration of a vaulted 2, 2'-binaphthol and a vaulted 3, 3'-biphenanthrol (VAPOL)

…, SM Yeung, RL Ostrander, AL Rheingold

Index: Bao, Jianming; Wulff, William D.; Dominy, James B.; Fumo, Michael J.; Grant, Eugene B.; Rob, Alexander C.; Whitcomb, Mark C.; Yeung, Siu-Man; Ostrander, Robert L.; Rheingold, Arnold L. Journal of the American Chemical Society, 1996 , vol. 118, # 14 p. 3392 - 3405

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Citation Number: 5

Abstract

Two methods for the synthesis of vaulted biaryls were developed involving the reactions of carbene complexes with alkynes and the [2+ 2] cycloaddition of ketenes. The final step in the synthesis of 3, 3'-diphenyl-[2, 2'-binaphthalene]-1, 1'-diol (39) and 2, 2'-diphenyl-[3, 3'- biphenanthrene]-4, 4'-diol (47)(VAPOL) was phenol coupling of the 3-phenyl-1-naphthol (14) and the 2-phenyl-4-phenanthrol (28), respectively. The naphthol 14 could be ...