13448-80-1

Upstream product

• 13113-71-8 (S)-Atrolactic acid 
• 186581-53-3 diazomethane 
• 24256-91-5 (S)-2-hydroxy-2-phenylbutanoic acid 
• 67-56-1 methanol 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 544-97-8 dimethyl zinc(II) 
• 74-88-4 methyl iodide 
• 69489-14-1 (S)-(+)-2-hydroxy-2-phenylpropanal 
• 115156-57-5 (2S,4aS,7R,8aR)-2-benzoyl-N-benzyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 115156-58-6 (S)-1-((2S,4aS,7R,8aR)-3-Benzyl-4,4,7-trimethyl-octahydro-benzo[e][1,3]oxazin-2-yl)-1-phenyl-ethanol 
• 128854-60-4 (S)-methyl mandelyl tetrahydropyranyl ether 
• 1448000-07-4 C₁₈H₂₂O₅ 
• 124-41-4 sodium methylate 
• 1448000-10-9 (3R,6S)-3-butyl-3-hexanoyl-6-methyl-6-phenyl-1,4-dioxane-2,5-dione 

Downstream Products

• 13113-71-8 (S)-Atrolactic acid 
• 2406-22-6 (2S)-2-phenylpropane-1,2-diol 
• 1213228-98-8 C₁₇H₁₅NO₆ 
• 69160-04-9 (R)-2-Methoxy-2-phenyl-propan-1-ol 
• 84999-94-0 (R)-(-)-cinnamyl 2-methoxy-2-phenylpropyl ether 
• 84999-95-1 (2R)-2-methoxy-2-phenylpropyl (Z)-3-phenyl-1-butenyl ether 
• 84999-99-5 C₂₂H₂₆O₂ 
• 84999-96-2 C₂₁H₂₆O₂ 
• 84999-98-4 C₂₂H₂₈O₂ 
• 84999-97-3 C₂₃H₃₀O₂ 
• 5933-41-5 methyl (S)-2-amino-2-phenylpropanoate 
• 627076-70-4 (R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate 
• 3966-30-1 (R)-Atrolactic acid 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 

Relevant academic research and scientific papers

Enantioselective addition of dimethylzinc to α-keto esters

The readily available (+)-N-Benzyl-(S)-mandelamide catalyzes the enantioselective addition of dimethylzinc to α-keto esters to give α-methyl-α-hydroxy esters containing stereogenic quaternary centers with moderate to good yields (56-87%). A good enantioselectivity of the reaction is obtained for aryl and heteroaryl keto esters. For these substrates ee values of 75-90% are obtained. The enantioselectivity is somewhat lower for the substrates bearing an aliphatic chain. Georg Thieme Verlag Stuttgart.

Catalytic asymmetric addition of dimethylzinc to α-ketoesters, using mandelamides as ligands

A strategy based on the control of the electron-donating capabilities of the coordinating groups of the ligand has been applied in the catalytic asymmetric addition of organometallic reagents to ketoesters. Mandelamides having deprotonated alcohol and carboxyamido groups catalyzed the addition of dimethylzinc to α-ketoesters with good yields and ee (up to 90%).

Multicenter Strategy for the Development of Catalytic Enantioselective Nucleophilic Alkylation of Ketones: Me2Zn Addition to α-Ketoesters

An array of heteroatoms is essential for the activity and enantioselectivity of the catalyst 2 in the addition of Me2Zn to α-ketoesters 1 (e.g. see equation). α-Hydroxyesters 3 were obtained with up to 96% ee in the presence of a catalytic amount of additive iPrOH, which serves to generate the catalytically active monomeric species (based on the observation of nonlinear effects).

A concise synthesis of (S)-(+)-1-(4-{2-[bis-(4-fluorophenyl)methoxy]-ethyl} piperazin-1-yl)-2-phenylpropan-2-ol dimaleate

(S)-(+)-1-(4-{2-[Bis-(4-fluorophenyl)methoxy]-ethyl}piperazin-1-yl) -2-phenylpropan-2-ol dimaleate was prepared in several steps from (S)-(+)-atrolactic acid by a process permitting synthesis of multigram quantities. With the information provided by asymmetric synthesis, the X-ray crystal structure was solved.

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol

The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts.

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage

The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C-F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditio

Asymmetric Ti-crossed Claisen condensation: Application to concise asymmetric total synthesis of alternaric acid

Asymmetric Ti-crossed Claisen condensation utilizing the dioxane-2,5-dione chiral template and its successful application to total synthesis of chiral alternaric acid are described.

Highly homogeneous stereocontrolled construction of quaternary hydroxyesters by addition of dimethylzinc to α-ketoesters promoted by chiral perhydrobenzoxazines and B(OEt)3

A highly efficient enantioselective addition of Me2Zn to α-ketoesters, assisted by a chiral perhydro-1,3-benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α-hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α-ketoesters are employed. The catalyst can be recovered and reused without loss of activity.