ASYMMETRIC 9-(1'-NAPHTHYL)FLUORENES - ENANTIOSELECTIVE SYNTHESIS, DETERMINATION OF ABSOLUTE-CONFIGURATION AND RETENTION OF AXIAL CHIRALITY IN THE FLUORENYL CARBANIONS

Authors
BAKER RW HAMBLEY TW TURNER P
Citation
Rw. Baker et al., ASYMMETRIC 9-(1'-NAPHTHYL)FLUORENES - ENANTIOSELECTIVE SYNTHESIS, DETERMINATION OF ABSOLUTE-CONFIGURATION AND RETENTION OF AXIAL CHIRALITY IN THE FLUORENYL CARBANIONS, Journal of the Chemical Society, Chemical Communications, (24), 1995, pp. 2509-2510
Citations number
14
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
24
Year of publication
1995
Pages
2509 - 2510
Database
ISI
SICI code
0022-4936(1995):24<2509:A9-ESD>2.0.ZU;2-A
Abstract
The rotamers of -methyl-9-[2'-(methoxymethyl)-1'-naphthyl]fluorene 10 and 11 were synthesised enantioselectively via ligand coupling reactio ns 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; deprotonati on of 10 and 11 affords fluorenyl carbanions, ent-12 and 12, respectiv ely, which retain axial chirality.