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.
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.
Morimoto
Toshiaki
T
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan. morimtt@u-shizuoka-ken.ac.jp
Yamazaki
Akira
A
Achiwa
Kazuo
K
D002384:Catalysis; D004164:Diphosphonates / Q000138:chemical synthesis* / Q000378:metabolism; D006865:Hydrogenation; D008024:Ligands; D009636:Norbornanes / Q000138:chemical synthesis* / Q000378:metabolism; D012238:Rhodium / Q000737:chemistry* / Q000378:metabolism
D004164:Diphosphonates; D008024:Ligands; D009636:Norbornanes; D012238:Rhodium