Axially Dissymmetric Bis(aminophosphine)s Derived from 2,2'-Diamino-1,1'-binaphthyl. Synthesis and Application to Rhodium(I)-Catalyzed Asymmetric Hydrogenations

Autor: Miyano, Sotaro, Nawa, Masayoshi, Mori, Akira, Hashimoto, Harukichi
Zdroj: Bulletin of the Chemical Society of Japan; August 1984, Vol. 57 Issue: 8 p2171-2176, 6p
Abstrakt: Axially dissymmetric bisphosphine ligands, (R)- and (S)-2,2'-bis(diphenylphosphinoamino)-1,1'-binaphthyl (BDPAB) and (R)-2,2'-bis[N-(diphenylphosphino)methylamino]-1,1'-binaphthyl (Me-BDPAB) were conveniently prepared from 2,2'-diamino-1,1'-binaphthyl. The rhodium(I)-catalyzed asymmetric hydrogenation of a-acylamidoacrylic acids and esters gave the corresponding amino acids of up to 95% optical purity. The sign of the centro-chirality of the product amino acids was always the same to that of the axial chirality of the ligand in both cases of BDPAB and Me-BDPAB.
Databáze: Supplemental Index