83023-81-8Relevant articles and documents
Enantioselective, chromatography-free synthesis of β3-Amino acids with natural and unnatural side chains
Gerfaud, Thibaud,Chiang, Ying-Ling,Kreituss, Imants,Russak, Justin A.,Bode, Jeffrey W.
scheme or table, p. 687 - 696 (2012/07/13)
β3-Amino acids are key components of some pharmaceuticals, excellent surrogates for metabolically labile α-amino acids, and building blocks for chiral heterocycles. Unfortunately they are not easily accessible in enantiomerically pure form, especially when possessing unnatural side chains. A flexible, chromatography-free process for the synthesis of enantiopure β3-amino acids possessing natural and unnatural side chains is described. The procedure uses inexpensive starting materials and reagents and offers a good alternative to the hazardous and expensive Arndt-Eistert homologation of enantiopure α-amino acids. Its utility has been demonstrated with the preparative scale synthesis of two valuable β3-amino acids possessing unnatural side chains.
Synthesis and Diels-Alder reactions of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and 2-alkyl-3-acyl-5-methylene-1,3-oxazolidin-4-ones: Highly exo and diastereoface selective chiral ketene equivalents
Roush,Essenfeld,Warmus,Brown
, p. 7305 - 7308 (2007/10/02)
Chiral dienophiles 1-3 undergo highly exo and diastereoface selective Diels-Alder reactions. The Diels-Alder reactions of 3 are also highly exo selective under Lewis acid catalyzed conditions.
Laboratory-Scale Enzymatic/Chemical Syntheses of D- and L-β-Chlorolactic Acid and D- and L-Potassium Glycidate
Hirschbein, Bernard L.,Whitesides, George M.
, p. 4458 - 4460 (2007/10/02)
This paper describes preparations of D- (and L-) chlorolactic acids having enantiomeric excesses greater than 97percent by D- (and L-) lactate dehydrogenase catalyzed reduction of chloropyruvic acid with NADH.In syntheses carried out on 0.1-0.5 mol scales