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Efficient 1,4-asymmetric induction utilizing electrostatic interaction between ligand and substrate in the asymmetric hydrogenation of didehydrodipeptides

1988; Issue: 7 Linguagem: Inglês

10.1039/p19880001787

2050-8255

Takamichi Yamagishi, Satoru Ikeda, Masanobu Yatagai, Motowo Yamaguchi, Mitsuhiko Hida,

Topic Modeling

Electrostatic interaction between the amino group of the achiral 3-dimethylaminopropylidenebismethylenebis(diphenylphosphine)(1) and the carboxy group of the substrate enabled an effective 1,4-asymmetric induction in the RhI-catalysed hydrogenation of didehydrodipeptides, to give (S,S)- or (R,R)-products selectively. The selectivity reached up to 94% diastereoisomeric excess with acetyl didehydrodipeptides and 92% with benzyloxycarbonyl substrates.