Highly stereoselective asymmetric hydrogenation of 2-benzamidomethyl-3-oxobutanoate catalysed by cationic binap–ruthenium(II) complexes
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 9,p. 609-610
- https://doi.org/10.1039/c39910000609
Abstract
Highly diastereoselective hydrogenation of methyl 2-benzamidomethyl-3-oxobutanoate has been accomplished by using [Rul{(R)-binap}(p-cymene)]I and corresponding complexes of derivatives of binap as catalyst, giving methyl (2S,3R)-2-benzamidomethyl-3-hydroxybutanoate, a versatile intermediate for the synthesis of β-lactam antibiotics, in up to 98% diastereoisomeric excess and 99% enantiomeric excess.Keywords
This publication has 10 references indexed in Scilit:
- Iridium(III) hydride complexes for the catalytic enantioselective hydrogenation of iminesJournal of the American Chemical Society, 1990
- BINAP: an efficient chiral element for asymmetric catalysisAccounts of Chemical Research, 1990
- Ruthenium-catalyzed oxidation of amides and lactams with peroxidesJournal of the American Chemical Society, 1990
- Chemoselective hydrogenation of imines catalysed by Ir III complexesJournal of the Chemical Society, Chemical Communications, 1990
- Dynamic kinetic resolution in BINAP—ruthenium(II) catalyzed hydrogenation of 2-substituted 3-oxo carboxylic estersTetrahedron: Asymmetry, 1990
- Stereoselective hydrogenation via dynamic kinetic resolutionJournal of the American Chemical Society, 1989
- Synthesis of new cationic BINAP–ruthenium(II) complexes and their use in asymmetric hydrogenation [BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]Journal of the Chemical Society, Chemical Communications, 1989
- Rhodium(I)-catalysed asymmetric hydrogenation of iminesJournal of the Chemical Society, Chemical Communications, 1988
- Practical synthesis of (R)- or (S)-2,2'-bis(diarylphosphino)-1,1'-binaphthyls (BINAPs)The Journal of Organic Chemistry, 1986
- Synthesis of novel chiral ruthenium complexes of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and their use as asymmetric catalystsJournal of the Chemical Society, Chemical Communications, 1985