79546-40-0

Upstream product

• 79546-42-2 N-(phenylglyoxyl)-(S)-α-alanine methyl ester 
• 100-52-7 benzaldehyde 
• 157982-28-0 (1R)-S-ethyl [1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]-thioacetate 
• 25726-04-9 phenylglyoxylyl chloride 
• 157982-25-7 (1R)-tetrahydropyran-(2RS)-2-yl [(1R,3R)-1-(1,3-dithiane-1,3-dioxide-2-yl)-1-phenyl]methyl ether 
• 158060-53-8 (1R,3R)-1,3-dithiane-1,3-dioxide-2-[(1R)-1-phenyl]methanol 
• 199870-96-7 (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate 
• 67-56-1 methanol 

Downstream Products

• 79546-46-6 (S)-2-[2-Phenyl-2-(2,2,2-trifluoro-acetoxy)-acetylamino]-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of chiral depsipeptide building block via asymmetric hydrosilylation

Asymmetric hydrosilylation of N-(α-ketoacyl)-α-amino esters was performed, catalyzed by rhodium(I) complex of chiral 2-(2-pyridyl)-4-carbomethoxy-1,3-thiazolidine or Rh(PPh3)3Cl. The N-(α-hydroxyacyl)-α-amino esters were synthesized

trans-1,3-dithiane-1,3-dioxide; a chiral acyl anion equivalent. Enantioselective synthesis of α-hydroxy- carboxylic acids, esters, amides and ketones

The reaction of (R,R)-(+)-1,3-dithiane-1,3-dioxide with aldehydes has been carried out and the dithiane dioxide moiety elaborated further. (R,R)-(+)-1,3-Dithiane-1,3-dioxide gave highly diastereoselective addition products with benzaldehyde and 3,4- dimethoxybenzaldehyde and single diastereomers were isolated in 84 and 76% purified yields respectively. Under similar conditions cyclohexane carboxaldehyde gave an easily separable mixture of diastereomers in 86% total isolated yield. The adducts were transformed into protected S- ethyl α-hydroxythioesters in 95-100% ee via a Pummerer reaction and subsequent trans-thioesterification protocol using LiSEt. Using LiSEt little racemisation occurred even with aryl substituted thioesters. Further transformations of thioesters to various α-hydroxy carboxylic acid derivatives (acids, esters, amides) without racemisation have been achieved. The approach resulted in the synthesis of the dimethyl ether of (R)-(-)-3,4-dihydroxymandelic acid in its naturally occurring form. Addition of dibutyl cuprate (derived from BuMgBr and Cu(I)Br) to the thioester gave the corresponding ketone in high yield and again without racemisation.

trans-1,3-Dithiane-1,3-Dioxide, a New Chiral Acyl Anion Equivalent for the Preparation of Masked Activated Acids: Application to the Synthesis of α-Hydroxy Acid Derivatives

trans-1,3-Dithiane-1,3-dioxide reacts with high diastereoselectivity with aromatic aldehydes and the 1,3-dithiane-1,3-dioxide moiety can be easily converted to a thiolester without racemisation by carrying out a Pummerer reaction; the thiolester is a group that can be readily transformed into acids, esters, amides, ketones and aldehydes.

Asymmetric hydrogenation of α-keto acid derivatives with Rh(I)-chiral diphosphinite system. Effect of halide counterion on the asymmetric induction

A chiral diphosphinite ligand having dicyclo-hexylphosphinooxy and dimethylamino moieties (Cy-POP-AE) was effective for the asymmetric hydrogenation of N-(benzoylformyl) amino acids by a Rh(I) catalyst under mild conditions. A neutral rhodium(I) precursor enabled a double asymmetric induction in methanol, while a cationic precursor caused an asymmetric induction controlled mainly by the substrate chirality.

Preparation of optically active peralkyldiphosphines and their use, as the rhodium(I) complex, in the asymmetric catalytic hydrogenation of ketones

Two types of the optically active peralkyldiphosphine, 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(dialkylphosphino)butane (Rdiop 3) and N-(N'-substituted carbamoyl)-4-dicyclohexylphosphino-2-dicyclohexylphosphinomethylpyrrolidine (R-Cycapp 8), have been p

ASYMMETRIC HYDROGENATION OF N-(α-KETOACYL)-α-AMINO ESTERS

Asymmetric hydrogenation of N-(α-ketoacyl)-α-amino esters with Cydiop-rhodium(I) complex catalysts produced optically active N-(α-hydroxyacyl)-α-amino esters in high optical yields, which may be useful as building blocks of depsipeptides.Almost no influen

SYNTHESIS OF CHIRAL OLIGOPEPTIDES BY MEANS OF CATALYTIC ASYMMETRIC HYDROGENATION OF DEHYDROPEPTIDES

Asymmetric hydrogenation of Ac-ΔTyr(Ac)-(S)-Ala-Gly-OMe (6), Ac-ΔTyr(Ac)-(R)-Ala-Gly-(S)-Phe-OMe (7), Ac-ΔPhe-NH-CH(R)-CH2-OCH2Ph (10), HCO-ΔPhe-(S)-Leu-OMe (16), X-AA-ΔPhe-AA'-OMe ( 5: X=tBOC, CBZ, CF3CO; AA, AA'= α-amino acid ), and t

SYNTHESIS OF CHIRAL DEPSIPEPTIDE BUILDING BLOCK BY THE ASYMMETRIC REDUCTION OF N-(α-KETOACYL)-α-AMINO ESTERS

Asymmetric reduction of N-(α-ketoacyl)-α-amino esters was performed by using homogeneous hydrosilylation and hydrogenation catalyzed by rhodium(I) complexes.The asymmetric hydrosilylation achieved good to high stereoselectivities giving the corresponding