S. Miyano, S. Handa, Kunitoshi Shimizu
Jul 1, 1984
Citations
0
Influential Citations
30
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The copper-promoted Ullmann reaction of chiral diol diesters of 1-bromo-2-naphthoic acid induced axial dissymmetry into the newly formed 1,1′-binaphthyl bond: chiral diol, apparent net optical yield for the joining of two naphthyl units, and axial chirality induced are as follows: (S)-1,1′-binaphthyl-2,2′-diol, 71%, S; (1S,2S)-1,2-diphenyl-1,2-ethanediol, 32%, S; (1R,2R)-1,2-bis(ethoxycarbonyl)-1,2-ethanediol, 33%, S; (4S,5S)-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane, 3.7%, R. The reaction of (R)-1,1′-binaphthyl-2,2′-diol esters of 2-halo-3-nitrobenzoic acids gave up to 85% net optical yield for the coupling; the intramolecular cyclization proceeded with virtually complete diastereoselectivity to give cyclic diester of R,R-configuration in a 42% isolated yield. This remarkable stereocontrol is ascribed to the steric requirement of the 12-membered cyclic diester structure containing rigid 1,1′-binaphthyl and 1,1′-biphenyl moiety.