109075-04-9

Upstream product

• 88452-86-2 (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 
• 70-55-3 toluene-4-sulfonamide 
• 109075-06-1 (S)-2-((4R,5R)-2,2-dimethyl-5-((S)-1-tosylaziridin-2-yl)-1,3-dioxolan-4-yl)-1-tosyl-aziridine 
• 1492-24-6 L-2-aminobutyric acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 109075-03-8 1,2,5,6-tetradeoxy-1,6-dimethyl-2,5-bis-L-iditol 
• 917-54-4 methyllithium 

Downstream Products

• 1492-24-6 L-2-aminobutyric acid 
• 93380-05-3 methyl 2(S)-butanoate 

Relevant academic research and scientific papers

Expanding the Protecting Group Scope for the Carbonyl Olefin Metathesis Approach to 2,5-Dihydropyrroles

Chiral pyrrolidine derivatives are important building blocks for natural product synthesis. Carbonyl olefin metathesis has recently emerged as a powerful tool for the construction of such building blocks from chiral amino acid derivatives. Here, we demons

Copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols as an expedient route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines

A new efficient synthetic route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines that relies on copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols under mild and operationally straightforward conditions is

Synthesis of α-amino acids by reaction of aziridine-2-carboxylic acids with carbon nucleophiles

A variety of homochiral α-amino acids have been prepared in good yield via regioselective reaction of higher order cuprates with (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 4. The reaction was much less regioselective and low yielding when higher order cuprates were reacted with the more hindered aziridine carboxylic acid 30, the principal products being protected β-amino acids. Reaction of lithium trimethylsilylacetylide with the aziridine acid 30, however, gave a protected α-amino acid which was converted to the protected isoleucine ester 37. The Royal Society of Chemistry 2006.

Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor

(Chemical Equation Presented) A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-α-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

PROCESS FOR MAKING N-SULFONATED-AMINO ACID DERIVATIVES

This invention relates to a process for preparing optically active α -amino acid substrates which are used to make potent lethal factor (LF) inhibitors for the treatment of anthrax. This invention further relates to a process for synthesis of potent LF-inhibitors for the treatment of anthrax. Specifically, the invention concerns a novel, high-yielding and highly enantioselective asymmetric hydrogenation reaction of a tetrasubstituted ene-sulfonamide acid or ester.

Synthesis of α-Amino Acids by Ring Opening of Aziridine-2-carboxylates with Carbon Nucleophiles

Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N-para-toluenesulfonylaziridine-2-carboxylic acid (6, R=H) protected as the anion.This has been developed into a general and high yielding synthesis of optically pure α-amino acids containing one chiral centre.When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired α-amino acid.Reaction with higher order cuprates gave lower yields, the principal products being the protected β-amino acids (22) and (23).

Nucleophilic Opening of Chiral Bis(aziridines): A Route to Enantiomerically Pure α-Amino Aldehydes or Acids and Polysubstituted Piperidines

α-Amino aldehydes or acids can be obtained by nucleophilic opening of suitably protected chiral bis(aziridines) derived from D-mannitol.Nucleophiles consist of a wide range of organometallic and heteronucleophilic reagents.Reaction orientation toward bis-

DIASTEREOSPECIFIC SYNTHESIS OF DIAZIRIDINES FROM D-MANNITOL. ACCESS TO CHIRAL α-AMINOACIDS.

Nucleophilic opening of chiral diastereoisomeric diaziridines obtained from D-mannitol leads to precursors of D or L α-aminoacids (or aldehydes) and also provides a means of synthesizing polyhydroxylated piperidines.