6141-42-0

Upstream product

• 855208-55-8 2-(N-nitroso-hydrazino)-hexanoic acid ethyl ester 
• 616-05-7 2-bromohexanoic acid 
• 100-97-0 hexamethylenetetramine 
• 97611-56-8 ethyl N-(diphenylmethylene)-2-aminohexanoate 
• 3087-36-3 titanium (IV) ethoxide 
• 110449-51-9 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-aminohexanoate 
• 110449-42-8 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> <(2S)-2-(N,N'-di-tert-butoxycarbonyl)>hydrazinohexanoate 
• 104897-89-4 N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-1-trimethylsilanyloxy-hex-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 142-61-0 Hexanoyl chloride 
• 96864-08-3 <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> hexanoate 
• 64-17-5 ethanol 
• 140170-78-1 (R)-2-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester 
• 616-06-8 2-amino-hexanoic acid 
• 151369-43-6 trans-2,5-Di-n-butyl-3,6-diethoxy-2,5-dihydropyrazine 

Downstream Products

• 34603-91-3 2-(2-phenyl-thiazolidin-3-yl)-hexanoic acid ethyl ester 
• 61298-96-2 C₁₇H₂₄N₂O₅S 

Relevant academic research and scientific papers

Palladium-Catalyzed Allylic Alkylation of Aldimine Esters with Vinyl-Cyclopropanes to Yield α,α-Disubstituted α-Amino Acid Derivatives

A synthetically useful approach for the synthesis of functionalized α, α-disubstituted α-amino acid derivatives via palladium-catalyzed 1,7 addition of readily available aldimine esters to vinylcyclopropanes is reported. This methodology was operated under mild conditions, affording α-allylic α-amino esters in good to excellent yields and excellent regio- and stereoselectivity. This transformation displays broad functional-group tolerance and enantioselective allylic alkylation has also been realized using a chiral phosphine ligand to provide the desired product. (Figure presented.).

Design and synthesis of a s-triazene based asymmetric organocatalyst and its application in enantioselective alkylation

A very efficient chiral organocatalyst was prepared from the readily available cyanuric chloride. The asymmetric catalyst exhibited a highly enantioselective catalytic performance for the alkylation of a glycinate Schiff base, which provides a useful procedure for the enantioselective synthesis of structurally diverse natural and unnatural α-alkyl-α-amino acids.

Efficient synthesis of α-substituted amino acid ester: Alkylation and hydrogenation removal of Schiff's base protecting group

A general and efficient synthetic route to α-amino acids by alkylation of the sodium salt of Schiff base ester 1 has been described previously. The α-substituted ethyl glycinates 4a-g are prepared in excellent yield by a two-step sequence involving regios

2-(Ethoxycarbonylmethyl)-1H-naphtho[1,8-de]-1,2,3-triazine anion: A new glycine enolate equivalent

The titled triazine can be alkylated with LDA and a variety of alkyl halides: Subsequent reduction with aluminium amalgam cleaves the naphthotriazine moiety to afford substituted α amino acids in excellent overall yields; the sequence defines a novel methodology that can be applied under non-acidic and largely non-aqueous conditions. (C) 2000 Elsevier Science Ltd.

Synthesis of tert-Leucine and Related Amino Acids

The 2,5-dialkoxypyrazines 3a and b were prepared in three steps from methyl glycinate hydrochloride (1) in an overall yield of 18 and 63 percent.Upon the addition of lithium organyls to 3b and subsequent acid hydrolysis the ethyl glycinates rac-7 were obtained.Key Words: tert-Leucine / Amino acids / Glycine cation equivalents / Bislactim ether method

A New Chiral Glycine Synthon. Synthesis, X-Ray Structure of (-)-(2S,4R)-2-Ethoxycarbonyl-4-phenyl-1,3-oxazolidine and Diastereoselective Nucleophilic Ring Opening to (R)-Ethyl α-Amino Carboxylates.

Condensation of (R)-N-benzyl-2-phenylglycinol 1 with the methyl hemiacetal of ethyl glyoxylate leads to (2S,4R)-2-ethoxycarbonyl-4-phenyl-1,3-oxazolidine 2 as the major product, obtained as a pure enantiomer after column chromatography.Compound 2 is stereoselectively cleaved by dialkylzinc reagents, prepared from alkylmagnesium iodides and ZnCl2, with moderate to good d.e. (72-94 percent).These compounds, after separation by column chromatography and debenzylation by hydrogenolysis in the presence of 10percent Pd on carbon, lead to enantiomerically pure ethyl α-amino carboxylates with good chemical yields. Key words: Chiral Oxazolidines, alpha-amino Esters, Chiral Glycine Synthon, Ring Opening, Asymmetric Synthesis

ENANTIOSELECTIVE SYNTHESES OF α-AMINO ACIDS FROM 10-SULFONAMIDO-ISOBORNYL ESTERS AND DI-t-BUTYL AZODICARBOXYLATE

Successive treatment of chiral esters 7 with LDA/Me3SiCl and di-t-butyl azodicarboxylate/TiCl4 and Ti(OiPr)4 gave N,N-di-t-butoxycarbonylhydrazinoesters 11 which on deacylation, hydrogenolysis, transesterification and acidic hydrolysis furnished (2S)-α-amino acid hydrochlorides 13 in good overall yields, high enantiomeric purity and with efficient recovery of the alcohol auxiliary 4.Experimental evidence for the configuration and conformation of the intermediate O-silyl ketene acetals 1 is provided.