7042-30-0

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 103-26-4 Methyl cinnamate 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 107-59-5 tert-Butyl chloroacetate 
• 27593-40-4 tert-butyl 3-phenyloxirane-2-carboxylate 
• 1415392-14-1 (2S,3R)-tert-butyl 3-chloro-2-hydroxy-3-phenylpropanoate 
• 62148-70-3 tert-butyl 3-chloro-2-oxo-3-phenylpropionate 
• 14990-09-1 tert-butyl cinnamate 
• 60843-66-5 2,2-dimethyl-1-(3-phenyloxiran-2-yl)propan-1-one 
• 135980-98-2 t-butyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-phenylpropionate 

Downstream Products

• 136031-73-7 (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester 
• 135981-02-1 tert-butyl (2R,3R)-3-amino-2-hydroxy-3-phenylpropionate 

Relevant academic research and scientific papers

Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters

The dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse β-substituted-α- hydroxy carboxylic acid derivatives. Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective α-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of β-aryl- and β-chloro-α-keto esters.

3- and 4-uloses derived from N-acetyl- D -glucosamine: A unique pair of complementary organocatalysts for asymmetric epoxidation of alkenes

The 4-ulose and the 3-ulose, both derived in two steps from the α-methyl glycoside of N-acetyl-D-glucosamine (GlcNAc), act as organocatalysts in the asymmetric epoxidation of alkenes, with unprecedented complementary enantioselectivity. The best results are found with α,β-unsaturated esters as substrates, with enantiomeric ratios up to 90:10 and 11:89, respectively. Copyright

Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn

A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O-C/O-N/O-S bonds through a single electron transfer from zinc metal to the niobium-substrate complex due to the high oxophilic nature of the niobium species. The presence of adjacent radical-stabilizing groups is beneficial to epoxide substrates; however the similar prerequisite does not apply to sulfoxides and amine N-oxides, where a broad range of substrates are efficiently deoxygenated in excellent yields.

Solid sodium hydroxide - THF, convenient system for synthesis esters of glycidic acids by darzens condensation

Isopropyl- and tert-butylchloroacetate react with carbonyl compounds in the presence of powdered sodium hydroxide in THF, without a catalyst, giving substituted glycidates. The process is applied for preparation of glycidates from ketones, hitherto unavailable by phase-transfer catalyzed Darzens condensation.

Arabinose-derived ketones as catalysts for asymmetric epoxidation of alkenes

Readily available arabinose-derived ketones, containing a tunable butane-2,3-diacetal as the steric blocker, displayed increasing enantioselectivity (up to 90% ee) with the size of the acetal alkyl group in catalytic asymmetric epoxidation of trans-disubstituted and trisubstituted alkenes. The stereochemical communication between our ketone catalysts and the alkene substrates is mainly due to steric effect, and electronic effect involving π-π interaction between phenyl groups of substrate and of catalyst did not appear to be operative in our system.

Convenient synthesis of t-butyl Z-3-substituted glycidates under conditions of phase-transfer catalysis

Reactions of mixtures of t-butyl E- and Z-3-substituted glycidates 1a-h with 50% aq. sodium hydroxide and a catalyst, benzyltriethylammonium chloride, TEBAC in dichloromethane (phase-transfer catalysis, PTC) led to preferential hydrolysis of the E-isomers to afford pure (90-98%) t-butyl Z-3-substituted glycidates 1a-i in good yields; PTC cleavage of glycidates additionally substituted at C-2, 1g or C-3, 1h,i suggests that an aryl group in the Z isomers hampers attack of HO- on the carbonyl carbon atom. As described in the literature, the diastereoselective PTC synthesis of Z-3-substituted glycidates and glycidonitriles consists of fast hydrolysis of E isomers present in mixtures with Z ones.

Diastereoselective Darzens reactions of α-chloroesters, amides and nitriles with aromatic aldehydes under phase-transfer catalyzed conditions

The development of the highly diastereoselective catalytic synthesis of glycidic acid derivatives via Darzens reaction is described. The reaction of α-chloroesters and amides with aromatic aldehydes smoothly proceeds in the presence of a quaternary ammonium salt as a phase-transfer catalyst to give the corresponding cis and trans desired products in satisfactory yields, respectively.

Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones: Total synthesis of diltiazem and Taxol side-chain

Poly-L-leucine catalyses the asymmetric epoxidation of enones 1-6 efficiently in a non-aqueous medium to provide the epoxy ketones 7-12 (70-91% yield; 80 to ≥95% ee). The strategy was used to make diltiazem 16 and the Taxol side chain 23 in single enantiomer form.

Process for the preparation of (2R,3R)-cis)-β-phenylglycidic acid

A method for preparing β-phenylglycidic-(2R, 3R) acid optionally in the form of salt or ester by precipitation of the salt of the β-phenylglycidic-(2R,3R) acid with (+)-α-methylbenzylamine-(R) in a solution of a mixture of salts of cis and trans β-phenylglycidic acids with (+)-α-methylbenzylamine(R)- and the use of the resulting product for preparing taxol and its analogs.

A Novel Darzens-Type Reaction Promoted by Tributylstannylcarbamate

Stannylcarbamate 1 proved to be a selective agent for generating organotin(IV) enolates from α-halo ketones.Thus, a Darzens reaction was achieved under mild and neutral conditions.The reaction took place without any side reactions and even with aliphatic α-halo ketones bearing enolizable α'-hydrogens.Various types of α,β-epoxy ketones and esters were obtained in this one-pot reaction.The stereoselectivity of the reaction was influenced by changing the halogen substituent of the α-halo ketones and by additives.Moreover, the present method could be appliedto γ- and δ-halo ketones as enolate precursors, and five- and six-membered cyclic compounds were obtained.