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• 609-14-3 2-acetylpropanoic acid ethyl ester 
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Relevant academic research and scientific papers

Asymmetric synthesis of glutamate derivatives

Analogs of glutamic acid were synthesized through the asymmetric Michael reaction using chiral acyclic β-enaminoesters and various Michael acceptors. The influence of the alkoxy group of the enaminoesters and also the nature of the olefins in the presence

Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin

A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement.

An enantioselective total synthesis of (+)- and (-)-saudin. Determination of the absolute configuration

A short efficient enantioselective synthesis of both (+)- and (-)-saudin, a naturally occurring hypoglycemic diterpene, is described. This synthesis establishes the absolute configuration of natural (-)-saudin for the first time. The key steps include the

Michael reaction of acyclic β-enaminoesters derived from α-alkyl-β-ketoesters and chiral α-methylbenzylamine: Stereoselective generation of quaternary carbon centres

Michael reaction of electrophilic olefins with acyclic β-enaminoester substrates derived from α-substituted β-ketoesters and (R)- or (S)-α-methylbenzylamine under neutral conditions resulted in the enantioselective formation of quaternary centres. The add

Easy access to optically active Hagemann's esters

The synthesis of optically active Hagemann's esters was investigated. The starting materials in this approach were enamino esters (R,Z)-8, prepared through the condensation of keto ester 6 with (R)-1-phenylethylamine 7. Michael addition reaction of the en

Condensation of chiral imines and chiral β-enaminoesters with maleic and citraconic anhydrides

Condensations of chiral imines 1 and 4, and chiral enaminoesters 10 and 13, with maleic and citraconic anhydrides were reported. These experimental outcomes can be rationalized by invoking the compact, endo-approaches of the two reactions 18.

Asymmetric formation of quaternary centers through aza-annulation of chiral β-enamino esters with acrylate derivatives

The aza-annulation of β-enamino ester substrates with acrylate derivatives was used for the stereoselective formation of quaternary carbon centers. Tetrasubstituted secondary enamines, in which the enamine tautomer was stabilized through conjugation with