143956-10-9

Upstream product

• 630-19-3 pivalaldehyde 
• 131791-76-9 cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one 
• 98-88-4 benzoyl chloride 
• 143870-65-9 1-benzoyl-2(S)-tert-butyl-6(S)-carboxy-perhydropyrimidin-4-one 
• 139119-52-1 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one 
• 74-88-4 methyl iodide 

Downstream Products

• 183182-01-6 (2S,5S)-1-Benzoyl-2-tert-butyl-3,5-dimethyl-tetrahydro-pyrimidin-4-one 

Relevant academic research and scientific papers

Enantioselective synthesis of β-amino acids. 7. Preparation of enantiopure α-substituted β-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

Inexpensive natural α-amino acid L-asparagine was efficiently converted to either (R)- or (S)-α-alkylated β-amino acids in enantiomerically pure state. The key intermediate in this protocol is the enantiopure N,N-acetal pyrimidinone (S)-1, a masked chiral derivative of β-alanine.

Preparation and Assignment of Configuration of 1-Benzoyl-(2S)-tert-butyl-3-methyl-perhydropyrimidin-4-one. Useful Starting Material for the Enantioselective Synthesis of α-Substituted β-Amino Acids

(S)-Asparagine, an inexpensive β-amino acid was converted into the title heterocycle (+)-1 in very good overall yield.The highly selective trans methylation of (+)-1-Li, and the hydrolysis of the resulting adduct afforded (R)-α-methyl-β-alanine, allowing the assignment of the (S) configuration in (+)-1.