Synthesis of Optically Active P-Chirogenic Ferrocene-Fused Benzophosphole by Diastereoselective Intramolecular Cyclization of Phosphanylferrocene Derivatives

Abstract

A novel optically active P-chirogenic ferrocene-fused benzophosphole, (S Fc ,R P )-4-phenylbenzo[b]ferroceno[d]phosphole, was synthesized by diastereoselective intramolecular cyclization of (S Fc )-1-(diphenylphosphanyl)-2-(2-lithiophenyl)ferrocene intermediates in two routes. The geometry of the new P-chirogenic ferrocenophosphole including absolute configuration of the phosphorous was disclosed by single crystal X-ray analysis of the palladium complex derived from the reaction of the phosphole with di-μ-dichloro-bis{2-[(dimethylamino)methyl]phenyl-C 1 ,N}dipalladium (II).

Synthetic Strategies for Accessing Dibenzophosphole Scaffolds

“…Similar cyclizations of lithio-biphenylphosphines were also observed when the species was generated from halobiphenyl-2-ylphosphines through halogen–lithium exchange (Scheme 37 ). 53 54 Related studies have been reported by Kurita and co-workers, 55 Xiao and co-workers, 56 and Hayashi and co-workers. 57…”