ChemInform Abstract: Axially Chiral Cyclopentadienyl Ligands: Stereoselective Synthesis of 1-Substituted-9-(1′-naphthyl)fluorenes and Retention of Axial Chirality in the Fluorenyl Carbanions.

✍ Scribed by R. W. BAKER; M. A. FOULKES; J. A. TAYLOR

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 41 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199828040

✦ Synopsis

1998 stereochemistry stereochemistry (general, optical resolution) O 0030

28 -040

Axially Chiral Cyclopentadienyl Ligands: Stereoselective Synthesis of 1-Substituted-9-(1'-naphthyl)fluorenes and Retention of Axial Chirality in the Fluorenyl Carbanions.

-Some in situ generated 1-substituted fluorenyllithiums are coupled with chiral sulfoxides to give single rotamers of type (III) and (VI) where the naphthalene ester substituent is syn to the fluorene 9-H. The stereoselectivity of the reaction is dependent on the sulfoxide, the fluorene substituent, and the temperature. The stereomutation of (+ac(R)-VIII) into its enantiomer (-ac(S)-VIII) demonstrates the retention of axial chirality in the fluorenyl carbanion. -(BAKER, R. W.;