292618-95-2

Upstream product

• 145057-94-9 (R)-2-<(2-hydroxy-1-phenylethyl)amino>propanenitrile 
• 56613-80-0 D-2-phenylglycinol 
• 100-39-0 benzyl bromide 

Downstream Products

• 292618-97-4 (1'S,3S,5R)-4-benzyl-3-(1'-hydroxybutyl)-3-methyl-5-phenylmorpholin-2-one 
• 147700-92-3 (3S,5R)-N,3-dibenzyl-3-methyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one 
• 292618-98-5 (3R,5R)-(4-benzyl-3-methyl-2-oxo-5-phenylmorpholin-3-yl)acetic acid, methyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of α,α-disubstituted amino acids by diastereoselective functionalization of enantiopure phenyloxazinones, derivatives of asymmetric Strecker reaction products of aldehydes

Esterification of the asymmetric Strecker reaction products of a suitable aldehyde and (R)-phenylglycinol followed by lactonization and alkylation provides chiral oxazinones 5. Treatment of the enolates of 5 with active alkyl halides, or aldehydes provided the corresponding functionalization products with high diastereoselectivity. The configuration of newly created quaternary carbon is S for the products coupled with simple alkyl halides and aldehydes, and R for the products coupled with methyl bromoacetate. Deprotection of these products afforded the corresponding enantiopure α,α-dialkyl amino acids.

Synthesis of enantiopure α,α-disubstituted amino acids from the asymmetric strecker reaction products of aldehydes

(equation presented) Treatment of the enolates of 4 generated from the asymmetric Strecker reaction products with alkyl halides or aldehydes provided the corresponding functionalized products with high diastereoselectivity. Deprotection of these products