Synthesis and optical resolution of 9,9'-spirobifluorene-1,1'-diol

Xu Cheng; Guo-Hua Hou; Jian-Hua Xie; Qi-Lin Zhou

doi:10.1021/ol0492546

Synthesis and optical resolution of 9,9'-spirobifluorene-1,1'-diol

Org Lett. 2004 Jul 8;6(14):2381-3. doi: 10.1021/ol0492546.

Authors

Xu Cheng¹, Guo-Hua Hou, Jian-Hua Xie, Qi-Lin Zhou

Affiliation

¹ State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.

PMID: 15228284
DOI: 10.1021/ol0492546

Abstract

[reaction: see text] 9,9'-Spirobifluorene-1,1'-diol (SBIFOL) was conveniently synthesized from 1,2-dibromobenzene and 3-bromoanisole in high yield. Both enantiomers of SBIFOL were obtained in 99% ee by inclusion resolution with 2,3-dimethoxy-N,N,N',N'-tetracyclohexylsuccinamide. The absolute configurations were determined by X-ray analysis of a single crystal of molecular complex.