83461-64-7

Upstream product

• 86448-81-9 Acetic acid (1R,2R)-2-methylsulfanyl-1-phenyl-2-((S)-toluene-4-sulfinyl)-ethyl ester 
• 86448-80-8 Acetic acid (1R,2R)-1-phenyl-2-((S)-toluene-4-sulfinyl)-2-p-tolylsulfanyl-ethyl ester 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 148312-55-4 tert-butyl thiazolidine-3-carboxylate 
• 752212-30-9 (1'R,2R)-tert-butyl 2-(1-acetoxy-1-phenylmethyl)thiazolidine-3-carboxylate 
• 1074-12-0 phenylglyoxal hydrate 
• 93-89-0 benzoic acid ethyl ester 
• 78549-07-2 (1R,2R,3S)-1-phenyl-2-p-tolylthio-2-p-tolylsuphinylethanol 
• 86448-59-1 2-Methylsulfanyl-1-phenyl-2-((S)-toluene-4-sulfinyl)-ethanone 
• 186414-21-1 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester 
• 186414-27-7 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester 
• 676328-56-6 (1R,2S)-2-(tert-butylthio)-1-phenyl-2-(2-pyridylthio)ethanol 
• 676328-67-9 (1R,2S)-1-acetoxy-2-(t-butylthio)-1-phenyl-2-(2-pyridylthio)ethane 

Downstream Products

• 34025-29-1 (R)-2-hydroxy-2-phenylacetaldehyde 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 

Relevant academic research and scientific papers

Enantioselective Reaction of α-Lithiated Dithioacetals Using Chiral Bis(oxazoline)s: New Chiral Formyl Anion Equivalents

The enantioselective reaction of various α-lithiated dithioacetals with aldehydes or a ketone in the presence of bis(oxazoline)s was examined. Among them, unsymmetrical dithioacetals were found to be the best choice for attaining high enantioselectivity. The reaction of lithiated tert-butylthio-(2-pyridylthio)methane with aldehydes proceeded with good diastereoselectivity as well as with good enantioselectivity. The enantioselective reaction was shown to proceed through dynamic thermodynamic resolution. Mercury(II) chloride effected hydrolysis of the dithioacetal moiety of the products to 2-hydroxyaldehydes, which were directly reduced to give the optically active 1,2-diols.

Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalents

The reaction of lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine with benzophenone in the presence of (-)-sparteine afforded the products with up to 97% ee and 93% ee, respectively. The reaction with various aromatic and aliphatic aldehydes also afforded the products with high enantioselectivity and moderate diastereoselectivity. Each diastereomer could be converted to optically active diols. Consequently, lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine serve as chiral formyl anion equivalents. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.

Highly enantioselective reaction of lithiated N-Boc-thiazolidine: A new chiral formyl anion equivalent

Reaction of lithiated N-Boc-thiazolidine 1 with various aldehydes in the presence of (-)-sparteine afforded the products with up to 93% ee. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway. Each diastereomeric alcohol could be converted to the corresponding optically active 1,2-ethanediols.

Diastereoselective reduction of chiral N-tosyl 2-benzoyl-1,3-oxazines derived from D-glucose

Stereochemistry of reduction of the diastereomerically pure N-tosyl 2-benzoyl-1,3-oxazines prepared from D-glucose was investigated with various reducing agents. It was found that the stereachemical outcome is consistent with the Cram's chelation model where the ring oxygen atom is involved in chelation, not the tosyl oxygen as in the 5-membered oxazolidines.

AN EFFICIENT 1,3-ASYMMETRIC INDUCTION ACCOMPANIED WITH EPIMERIZATION AT THE 2-POSITION. STEREOSELECTIVE REDUCTION OF α-SUBSTITUTED β-KETO SULFOXIDES UNDER BASIC CONDITIONS

An efficient 1,3-asymmetric induction was realized in the reduction of β-keto sulfoxides having various α-substituents with NaBH4 under basic conditions and, by the application of this induction, (R)-α-acetoxyphenylacetaldehyde was synthesized.