97551-20-7

Upstream product

• 111199-07-6 (S)-2-hydroxy-3,N,N-trimethylbutanamide 
• 63935-93-3 benzoyltriethylsilane 
• 67-63-0 isopropyl alcohol 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 212896-13-4 (1S)-1-benzoyl-2-(tert-butoxycarbonylamino)-2-methylpropyl ethanoate 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 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]} 
• 278175-37-4 (3S,5R,6S)-3-isobutyl-6-isopropyl-4-methyl-5-phenyltetrahydro-2H-1,4-oxazin-2-one 

Relevant academic research and scientific papers

Synthesis of Chiral Alkenyl Cyclopropane Amino Acids for Incorporation into Stapled Peptides

α,α′-Disubstituted amino acids serve as important non-proteinogenic amino acids in the construction of stabilized helical peptides. To expand the repertoire of α,α′-disubstituted amino acids, chiral alkenyl-containing cyclopropane amino acids were synthes

BUILDING BLOCKS FOR STAPLED PEPTIDES

This invention relates to a method for producing an alkenyl 1 -aminocyclopropane-1 -carboxylic acid of Formula I wherein R1 is a protecting group, n is an integer between 1 and 10, and A and B are chiral centres such that when A is S, B is R an

Metallophosphites as Umpolung Catalysts: The Enantioselective Cross Silyl Benzoin Reaction

Carbonyl polarity reversal (umpolung) has been realized employing metallophosphites as catalysts. As a result, nonenzymatic asymmetric cross silyl benzoin reactions have been achieved, giving optically active silyl ether-protected benzoin adducts. The reaction is general with respect to aryl, alkyl, and heterocyclic substrates with good to excellent yields and good to excellent enantioselectivities. Copyright

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 substituted 1-aminocyclopropane-1-carboxylic acids from a new chiral glycine equivalent with 3,6-dihydro-2H-1,4-oxazin-2- one structure

Condensation of the new chiral glycine equivalent 10 with aldehydes at room temperature in the presence of K2CO3 under solid-liquid phase- transfer-catalysed conditions afforded stereoselectively new chiral (Z)- α,β-didehydroamino ac