Preparation of Enantiopure Norbornane Ligands Bearing Both (2S,3S)-Bis(phosphinomethyl) and 7-syn-Oxygen Functional Groups and an Application to Rhodium-Catalyzed Asymmetric Hydrogenation

Toshiaki Morimoto; Akira Yamazaki; Kazuo Achiwa

doi:10.1248/cpb.52.1367

Notes

Preparation of Enantiopure Norbornane Ligands Bearing Both (2S,3S)-Bis(phosphinomethyl) and 7-syn-Oxygen Functional Groups and an Application to Rhodium-Catalyzed Asymmetric Hydrogenation

Toshiaki Morimoto, Akira Yamazaki, Kazuo Achiwa

著者情報

キーワード: chiral norbornane, diphosphine ligand, asymmetric hydrogenation, diastereoselective Diels–Alder reaction, stereospecific rearrangement, rhodium

ジャーナルフリー

2004 年 52 巻 11 号 p. 1367-1371

DOI https://doi.org/10.1248/cpb.52.1367

詳細

抄録

Enantiopure bicyclo[2.2.1]heptane derivatives having both (2S,3S)-bis[(diphenylphosphino)methyl] and 7-syn-oxygen functional groups were synthesized by using diastereoselective Diels–Alder reaction of di-(1R)-menthyl fumarate and 5-trimethylsilylcyclopentadiene followed by silver-promoted stereospecific frame rearrangement of a bromolactone intermediate. Rhodium-catalyzed asymmetric hydrogenations were carried out using the diphosphines as a chiral ligand.

責任著者(Corresponding author)

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