Concepedia

(5S)-5-benzyl-2,2,3-trimethylimidazoiidin-4-one as a highly effective chiral auxiliary for asymmetric reduction of α-oxo amides

Igor Solodin, Yuri Goldberg, Gunārs Zelčāns, E. Lukevics

Journal of the Chemical Society Chemical Communications · 1990 · 27 citations · 10 references

DOI

Concepts

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.

References

10

Asymmetric Organic Reactions

Chemical & Engineering News · 1977 · 525 citations

, , +20

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 alkanones

Makoto Fujita, Tamejiro Hiyama · The Journal of Organic Chemistry · 1988 · 169 citations

, , +14

Reduction of carbonyl compounds via hydrosilylation. 3. Asymmetric reduction of keto esters via hydrosilylation catalyzed by a rhodium complex with chiral phosphine ligands

Iwao Ojima, Tetsuo Kogure, Miyoko Kumagai · The Journal of Organic Chemistry · 1977 · 103 citations

, , +13

Stereoselective alkylation of glycine units in dipeptide derivatives. "Chirality transfer" via a pivalaldehyde N,N-acetal center

Robin Polt, Dieter Seebàch · Journal of the American Chemical Society · 1989 · 58 citations

, , +16

Mechanism of the reduction of ketones by trialkylsilane. Hydride transfer, SET-hydrogen atom abstraction, or free radical addition

Dan Yang, Dennis D. Tanner · The Journal of Organic Chemistry · 1986 · 56 citations

, , +18