191406-50-5

Upstream product

• 5848-60-2 (E)-1-phenyl-3-(phenylthio)propene 
• 35059-50-8 t-butyl diazoacetate 

Downstream Products

• 221082-33-3 (4S,3S)-4,5-epoxy-3-phenyl-1-pentene 
• 221082-32-2 (2R,3S)-3-phenyl-2-phenylthio-4-penten-1-ol 

Relevant academic research and scientific papers

Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

Reaction of allyl aryl sulfides and α-diazoacetic acid esters in the presence of optically active Co(III)-salen complex (8-Br) provided 3- substituted 2-arylthio-4-pentenoic acid esters stereoselectively by way of enantioselective S-ylide formation and subsequent diastereoselective [2,3]sigmatropic rearrangement. For example, the reaction of cinnamyl phenyl sulfide and (-)-menthyl α-diazoacetate provided (-)-menthyl (2R,3S)-2- phenylthio-3-phenyl-4-pentenoate of 74% de preferentially.

Co(III)-salen catalyzed carbenoid reaction: Stereoselective [2,3]sigmatropic rearrangement of S-ylides derived from allyl aryl sulfides

Allyl aryl sulfides and diazoacetic acid esters react in the presence of optically active Co(III)-salen complex (4) with good enantioselectivity, to give the [2,3]sigmatropic rearrangement products, 2-arylthio-3-aryl-4-pentenoic acid esters, via the corresponding S-ylides.