83461-63-6

Upstream product

• 86448-80-8 Acetic acid (1S,2S)-1-phenyl-2-((S)-toluene-4-sulfinyl)-2-p-tolylsulfanyl-ethyl ester 
• 78549-08-3 (1S,2S,3S)-1-phenyl-2-p-tolylthio-2-p-tolylsulphinylethanol 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 148312-55-4 tert-butyl thiazolidine-3-carboxylate 

Relevant academic research and scientific papers

Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates to Deliver Quaternary Stereocenters

Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.

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.

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.