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Paper | Regular issue | Vol 78, No. 12, 2009, pp.3001-3010
Published online, 28th September, 2009
DOI: 10.3987/COM-09-11812
Synthesis of Optically Active P-Chirogenic Ferrocene-Fused Benzophosphole by Diastereoselective Intramolecular Cyclization of Phosphanylferrocene Derivatives

Shuji Yasuike, Jun-ichi Hagiwara, Hiroshi Danjo, Masatoshi Kawahata, Naoki Kakusawa, Kentaro Yamaguchi, and Jyoji Kurita*

*Faculty of Pharmaceutical Sciences, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan

Abstract

A novel optically active P-chirogenic ferrocene-fused benzo- phosphole, (SFc,RP)-4-phenylbenzo[b]ferroceno[d]phosphole, was synthesized by diastereoselective intramolecular cyclization of (SFc)-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-C1,N}dipalladium (II).