Journal of the Chemical Society, Chemical Communications
Journal of the Chemical Society, Chemical Communications was published between 1972 - 1995.
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Paper
J. Chem. Soc., Chem. Commun., 1995, 2509 - 2510, DOI: 10.1039/C39950002509
Asymmetric 9-(1
-naphthyl)fluorenes: enantioselective synthesis, determination of absolute configuration and retention of axial chirality in the fluorenyl carbanionsRobert W. Baker, Trevor W. Hambley and Peter Turner
The rotamers of 1-methyl-9-[2
-(methoxymethyl)-1-naphthyl]fluorene 10 and 11 were synthesised enantioselectively via ligand coupling reactions of 1-(alkyl or arylsulfinyl)naphthalene-2-carboxylate esters with 1-methylfluorenyllithium and the absolute configurations established by a single crystal X-ray study of the (1R)-menthyl ester 4; deprotonation of 10 and 11 affords fluorenyl carbanions, ent-12 and 12, respectively, which retain axial chirality.
