50774-77-1

Upstream product

• 821-06-7 (E)-1,4-dibromobutene 
• 100-58-3 phenylmagnesium bromide 
• 6052-63-7 2-phenylbut-3-en-1-ol 

Downstream Products

• 939799-53-8 diethyl 2-phenylbut-3-enylphosphonate 
• 111462-83-0 tert-Butyl-(2-phenyl-but-3-enyl)-amine 
• 36617-88-6 (R)-3-phenyl-1-butene 
• 58717-85-4 (S)-3-phenyl-1-butene 
• 939799-58-3 (2S,1'S,2'R,3'R)-N-[(R)-α-phenylglycinyl]-2-[2'-diethylphosphono-3'-phenylcyclopropyl]glycinonitrile 
• 939799-57-2 (2S,1'R,2'S,3'S)-N-[(R)-α-phenylglycinyl]-2-[2'-diethylphosphono-3'-phenylcyclopropyl]glycinonitrile 
• 939799-54-9 diethyl 2-oxiran-2-yl-2-phenylethylphosphonate 

Relevant academic research and scientific papers

Enantioselective iridium-catalyzed allylic arylation

We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.

High diversity on simple substrates: 1,4-dihalo-2-butenes and other difunctionalized allylic halides for copper-catalyzed SN2′ reactions

Enantioselective allylic alkylation with an organomagnesium reagent catalyzed by copper thiophene carboxylate (CuTC) was carried out on difunctionalized substrates, such as commercially available 1,4-dichloro-2- butene and 1,4-dibromo-2-butene, and on similar compounds of higher substitution pattern of the olefin for the formation of all-carbon chiral quaternary centers. The high regioselectivity obtained throughout the reactions favored good regiocontrol for the addition of phenyl Grignard reagents. Other difunctionalized substrates (allylic ethers and allylic alcohols) also underwent asymmetric SN2′ substitution.

Synthesis and preliminary pharmacological evaluation of the four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine, the first class of 3′-substituted transC1′-2′-2-(2′-phosphonocyclopropyl)glyc ines

Four stereoisomers of (2S)-2-(2′-phosphono-3′-phenylcyclopropyl)glycine were synthesized by a stereocontrolled synthetic procedure and evaluated as mGluRs ligands. The (2S,1′R,2′S,3′R)-isomer (PPCG-2) showed to be a group III mGluRs selective ligand endow