(5S)-5-benzyl-2,2,3-trimethylimidazoiidin-4-one as a highly effective chiral auxiliary for asymmetric reduction of α-oxo amides
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 19,p. 1321-1322
- https://doi.org/10.1039/c39900001321
Abstract
Reduction of the α-oxo amide derived from phenylglyoxylic acid, containing (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one as a chiral auxiliary, with NaBH4 or via fluoride ion-induced hydrosilylation with HSiMe2Ph was found to proceed with 90–100% diastereoselectivity.Keywords
This publication has 11 references indexed in Scilit:
- Fluoride ion-induced hydrosilylation of aldehydes and ketones under phase-transfer conditionsJournal of Organometallic Chemistry, 1989
- Stereoselective alkylation of glycine units in dipeptide derivatives. "Chirality transfer" via a pivalaldehyde N,N-acetal centerJournal of the American Chemical Society, 1989
- Fluoride ion-catalyzed reduction of aldehydes and ketones with hydrosilanes. Synthetic and mechanistic aspects and an application to the threo-directed reduction of .alpha.-substituted alkanonesThe Journal of Organic Chemistry, 1988
- Herstellung enantiomerenreiner, α‐alkylierter Lysin‐, Ornithin‐ und Tryptophan‐DerivateHelvetica Chimica Acta, 1988
- Diastereoselective Reduction of α-Keto Amides Having trans-2,5-Disubstituted Pyrrolidines as Chiral AuxiliariesChemistry Letters, 1987
- Asymmetric Synthesis of the Both Enantiomers of α-Hydroxy Acids by the Diastereoselective Reduction of Chiral α-Keto Amides with (Complex) Metal Hydrides in the Presence of Metallic SaltChemistry Letters, 1986
- Asymmetric Heterogeneous Catalytic HydrogenationPublished by Elsevier ,1985
- Reduction of carbonyl compounds via hydrosilylation. 3. Asymmetric reduction of keto esters via hydrosilylation catalyzed by a rhodium complex with chiral phosphine ligandsThe Journal of Organic Chemistry, 1977
- “DOUBLE ASYMMETRIC REDUCTION” OF (−)MENTHYL BENZOYLFORMATE USING CATALYTIC HYDROSILYLATIONChemistry Letters, 1975
- Phenylalanyl transfer ribonucleic acid synthetase from Escherichia coli. Analysis of the phenylalanine binding siteBiochemistry, 1971