226949-82-2

Upstream product

• 109-72-8 n-butyllithium 
• 226949-79-7 (3S)-3-phenyl-2,3-dihydrooxazolo[3,2-a]pyrimidin-7-one 
• 165035-65-4 (4S)-4-phenyloxazolidin-2-ylidene amine 
• 20989-17-7 (2S)-2-phenylglycinol 

Downstream Products

• 252579-97-8 (3S,5S,6S)-5-butyl-6-methyl-3-phenyl-2,3,5,6-tetrahydrooxazolo[3,2-a]pyrimidin-7-one 
• 330983-41-0 (1'S,6S)-6-butyl-1-(1'-phenylethyl)dihydropyrimidin-2,4-dione 

Relevant academic research and scientific papers

A new chiral auxiliary derived from (2S)-phenylglycinol: An access to enantiomerically pure β-amino acids

A new bicyclic heterocycle 3, which is potentially useful for the synthesis of β-amino acids, has been obtained from a reaction between (S)- phenylglycinol and cyanogen bromide followed by a condensation with methyl propiolate. Conjugate additions of different organocuprate reagents to this chiral Michael acceptor occurred with complete diastereoselectivity. An optically pure β amino acid was obtained in excellent yield from the masked chiral derivative 4a.

Enantioselective synthesis of α,β-substituted β-amino acids

Chiral derivative 3 was shown to be a precursor of α and β-substituted β-amino acids as well as α,β-disubstituted β-amino acids. The key steps of the procedure are a diastereoselective alkylation of synthon 3 by organocuprates reagents and a diastereoselective alkylation of the alkylated adduct.