Asymmetric 9-(1′-naphthyl)fluorenes: enantioselective synthesis, determination of absolute configuration and retention of axial chirality in the fluorenyl carbanions

Robert W. Baker; Trevor W. Hambley; Peter Turner

doi:10.1039/C39950002509

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Journal of the Chemical Society, Chemical Communications

Issue 24, 1995

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Asymmetric 9-(1′-naphthyl)fluorenes: enantioselective synthesis, determination of absolute configuration and retention of axial chirality in the fluorenyl carbanions

Robert W. Baker , Trevor W. Hambley and Peter Turner

J. Chem. Soc., Chem. Commun., 1995, 2509-2510

DOI: 10.1039/C39950002509

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Abstract
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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.

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Journal of the Chemical Society, Chemical Communications

Asymmetric 9-(1′-naphthyl)fluorenes: enantioselective synthesis, determination of absolute configuration and retention of axial chirality in the fluorenyl carbanions

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