139243-60-0Relevant academic research and scientific papers
Enantioselective Synthesis of β-Amino Acids. 5. Stereoselective Reaction of Chiral Pyrimidinone Enolates with Aldehydes
Murer, Peter,Rheiner, Beat,Juaristi, Eusebio,Seebach, Dieter
, p. 319 - 344 (2007/10/02)
Hydro-pyrimidinones ((2S,6R)-3) and ((2S)-6) were prepared from methyl crotonate via 3-aminobutanoate, and their corresponding lithium enolate and dienolate derivatives were added to various aldehydes.The high regio- and stereoselectivities observed in these aldol reactions pave the road for the preparation of enantiomerically pure β-hydroxy-β'-amino acids.The structures of the products were confirmed by X-ray crystal structure analysis (eight examples).
Enantioselective Synthesis of β-Amino Acids. 2. Preparation of the like Stereoisomers of 2-Methyl- and 2-Benzyl-3-aminobutanoic Acid
Juaristi, Eusebio,Escalante, Jaime,Lamatsch, Bernd,Seebach, Dieter
, p. 2396 - 2398 (2007/10/02)
An improved procedure for the preparation of (R)- and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the corresponding (1'S)-N-phenethyl derivatives 1 is reported.From 2a, the four possible stereoisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3.In the cyclization of 3, the cis products 4 predominate ca. 95:5.These heterocycles can be alkylated (LDA, RX), as demonstrated by methylation and benzylation, with formation of a single diastereoisomer (5, 6).Hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads to the free amino acids 7-10.
