Efficient 1,4-asymmetric induction utilizing electrostatic interaction between ligand and substrate in the asymmetric hydrogenation of didehydrodipeptides
Takamichi Yamagishi, Satoru Ikeda, Masanobu Yatagai, Motowo Yamaguchi, Mitsuhiko Hida · Journal of the Chemical Society Perkin Transactions 1 · 1988
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.