37866-55-0

Upstream product

• 1778-09-2 4-(Methylthio)acetophenone 

Downstream Products

• 1206967-39-6 C₉H₁₃NS 
• 186296-26-4 (S)-N-[1-(4-methylthiophenyl)ethyl]acetamide 
• 1434602-26-2 (E)-1-(4-methylthiopheneyl)ethanone O-benzyloxime 
• 134899-67-5 N-{1-[(E)-4-Methylsulfanyl-phenylimino]-ethyl}-3-nitro-N-(4-nitro-phenyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: Applications toward the synthesis of calcimimetic agents

Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.