228717-14-4

Upstream product

• 212896-13-4 (1S)-1-benzoyl-2-(tert-butoxycarbonylamino)-2-methylpropyl ethanoate 
• 736123-29-8 Amino-acetic acid (S)-1-benzoyl-2-methyl-propyl ester 
• 111199-07-6 (S)-2-hydroxy-3,N,N-trimethylbutanamide 
• 97551-20-7 S-(+)-1-phenyl-2-hydroxy-3-methylbutanone 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 33797-51-2 eschenmoser's salt 
• 212896-12-3 (6S)-6-isopropyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one 

Downstream Products

• 278175-34-1 (1S,2R,4S,6'S)-bicyclo[2.2.1]hept-5-en-2-spiro{3[6'-isopropyl-5'-phenyl-3',6'-dihydro-2'H-1',4'-oxazin-2'-one]} 

Relevant academic research and scientific papers

New Chiral Didehydroamino Acid Derivatives from a Cyclic Glycine Template with 3,6-Dihydro-2H-1,4-oxazin-2-one Structure: Applications to the Asymmetric Synthesis of Nonproteinogenic α-Amino Acids

New chiral (Z)-α,β-didehydroamino acid (DDAA) derivatives with 3,5-dihydro-2H-1,4-oxazin-2-one structure 11a-f have been stereoselectively prepared after condensation of chiral glycine equivalent 7 with aldehydes in the presence of K2CO3 under mild solid-liquid phase-transfer catalysis reaction conditions. These new systems have been used in diastereoselective cyclopropanation reactions using Corey's ylide for the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acids (ACCs) such as allo-corononamic and allo-norcoronamic acids. The hydrogenation reaction of these systems at ambient pressure in the presence of formaldehyde affords saturated oxazinones and N-methylated oxazinones which have been transformed into the N-methyl-α-amino acids (N-MAAs) (S)-2-(methylamino)butanoic acid and (S)-N-methylleucine. In addition, the parent α,β-didehydroalanine derivative 11g has been prepared by a direct aminomethylation-elimination sequence from 7 and Eschenmoser's salt and has been used in Diels-Alder cycloaddition with endo selectivity for the synthesis of the enantiomerically pure bicyclic α-amino acids (-)-2-aminobicyclo[2.2.1]heptane-2-carboxylic and (-)-2-aminobicyclo[2.2.2]octane-2-carboxylic acids.

Asymmetric synthesis of bicyclic α-amino acids by a Diels-Alder reaction to a new chiral α,β-didehydroalanine derivative

A new chiral cyclic α,β-didehydroalanine derivative, (6S)-6-isopropyl- 3-methylene-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one, has been prepared by in situ aminomethylation-elimination of a chiral glycine-derived precursor. This oxazin-2-one acts as a react