T. Morimoto*, A. Yamazaki, K. Achiwa
Apr 5, 2005
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Journal
ChemInform
Abstract
Enantiopure bicyclo[2.2.1]heptane derivatives having both (2 S ,3 S )-bis[(diphenylphosphino)methyl] and 7-syn -oxygen functional groups were synthesized by using diastereoselective Diels–Alder reaction of di-(1 R )-men-thyl 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.