107740-74-9

Upstream product

• 16537-09-0 t-butyl phenylacetate 
• 7332-98-1 tert-butyl phenylglyoxylate 
• 4768-42-7 tert-butyl (+/-)-O-acetylmandelate 
• 75716-83-5 tert-butyl α-oxo-1H-imidazole-1-acetate 
• 611-71-2 (R)-Mandelic Acid 
• 51019-43-3 (R)-(-)-O-acetylmandelic acid 
• 117356-18-0 β-hydroxy β-phenyl acetate de t-butyle 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 7633-32-1 tert-butyl glyoxylate 
• 98-80-6 phenylboronic acid 
• 13994-41-7 tert-butoxycarbonylmethyl nitrate 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 75-65-0 tert-butyl alcohol 
• 98-86-2 acetophenone 

Downstream Products

• 1194481-20-3 t-butyl N-(Phth)-(D)-aminoxymandelate 
• 117356-18-0 β-hydroxy β-phenyl acetate de t-butyle 

Relevant academic research and scientific papers

A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis

An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.

Controlled racemization and asymmetric transformation of α-substituted carboxylic acids in the melt

The racemization and asymmetric transformation of a series of α- substituted carboxylic acids, viz. mandelic acid, hydratropic acid, ibuprofen and naproxen, were studied. Several racemization methods for mandelic acid were studied and it was found that base-catalyzed racemization in aprotic polar solvents was the most efficient method. Moreover, a fast and mild base- catalyzed racemization reaction in the melt was developed. DBN turned out to be a very efficient racemizing base for the substrates studied. Combination of the base-catalyzed racemization in the melt with known resolution processes resulted in crystallization-induced asymmetric transformations. Treating racemic ibuprofen or hydratropic acid with 1.5-2.5 equivalents of enantiopure α-methylbenzylamine and a catalytic amount of DBN resulted in the isolation of enantiomerically enriched ibuprofen or hydratropic acid with ees of up to 75% and almost quantitative yields.

METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE

Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

Chiral N,N′-dioxide-FeCl3 complex-catalyzed asymmetric intramolecular Cannizzaro reaction

An environmentally benign catalyst, the N,N′-dioxide-FeCl3 complex, has been developed for the asymmetric intramolecular Cannizzaro reaction. Aryl and alkyl glyoxal monohydrates were applied to obtain α-hydroxy acid esters with excellent results. Deuterium-label and control experiments shed light on the reaction mechanism.

Enantio- and chemoselective Br?nsted-acid/Mg(nBu) 2 catalysed reduction of α-keto esters with catecholborane

The first enantio- and chemoselective Br?nsted-acid catalysed reduction of α-keto esters with catecholborane has been developed. The α-hydroxy esters were obtained under mild reaction conditions in virtually quantitative yields and excellent enantioselectivities. With slight modifications both enantiomers can be obtained without any loss of selectivity. This journal is the Partner Organisations 2014.

Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex

The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl2(PPh3)3 with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities. The Royal Society of Chemistry 2012.

Stereomodulating effect of remote groups on the NADH-mimetic reduction of alkyl aroylformates with 1,4-dihydronicotinamide-β-lactam amides

Conformationally restricted NADH peptidomimetics 4a-e, characterized by the presence of a (1,4-dihydronicotinamide)-(β-lactam) moiety, have been synthesized and used to study the Mg2+ cation-promoted asymmetric reduction of alkyl aroylformates

Chiral cobalt-catalyzed enantioselective aerobic oxidation of α-hydroxy esters

A chiral cobalt-catalyzed enantioselective aerobic oxidative kinetic resolution of (±)-α-hydroxy esters, using molecular oxygen as a sole oxidant, is reported and a maximum of selectivity factor (s) 31.9 was achieved with >99% enantiomeric excess for unreacted α-hydroxy esters.

3-Pyrroline-1-carbonyl (Pyroc) group: A removable protecting group for the kinetic resolution of racemic carboxylic acids and alcohols through catalytic asymmetric acylation

The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine

Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and α-aminoxy peptides

(Chemical Equation Presented) N-(Pg-α-aminoxy acids) 1a-g are converted to N-(Pg-α-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, α-amino acids/α-dipeptides, and α-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e′), and (3g+3g′), aminoxy hybrid peptides 4a-h, (4a+4a′), 6a-d, 9a-e, (9a+9a′), and (9b+9b′), and α-aminoxy peptides 10a,b in good yields without racemization. 2009 American Chemical Society.