Issue 24, 1995

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

Abstract

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.

Article information

Article type
Paper

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

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

R. W. Baker, T. W. Hambley and P. Turner, J. Chem. Soc., Chem. Commun., 1995, 2509 DOI: 10.1039/C39950002509

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements