130700-06-0

Upstream product

• 1823-14-9 5-phenyl-1-pentyne 
• 77877-57-7 6-phenyl-2-hexyn-1-ol 
• 10353-53-4 1,2-epoxy-5-hexene 
• 591-50-4 iodobenzene 

Downstream Products

• 139400-23-0 (1S,2R)-cis-1-(Hydroxymethyl)-2-(3'-phenylpropyl)cyclopropane 
• 139400-23-0 (1R,2S)-cis-1-(Hydroxymethyl)-2-(3'-phenylpropyl)cyclopropane 

Relevant academic research and scientific papers

Stereoselective Carbocyclization of Vinyloxiranes Catalyzed by Lewis Acids: Construction of the Musellarin Tricyclic Core

Stereoselective carbocyclizations of vinyloxiranes were efficiently catalyzed by Lewis acids to provide cyclic homoallyl alcohols as single isomers. The choice of Lewis acid, B(C6F5)3 was crucial for the stereoselective tr

Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen

Copper(I)–N-heterocyclic-carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H2) and their subsequent transfer to allylic chlorides. The highly chemoselective catalyst displayed no concomitant hydrogenation reactivity; in fact, the terminal double bond formed in the hydride transfer remained intact. Switching to deuterium gas (D2) allowed for regioselective monodeuteration with excellent isotope incorporation.

Iridium complex-catalyzed allylic alkylation of allylic esters and allylic alcohols: Unique regio- and stereoselectivity

An iridium complex was found to be an efficient catalyst for allylic alkylation of allylic esters with a stabilized carbon nucleophile. Highly regioselective alkylation at the substituted allylic terminus was achieved. The catalytic activity and regioselectivity were affected by the ligand used. The reaction of (E)-2-alkenyl acetates or 1-substituted 2-propeny acetates with dialkyl sodiomalonate in the presence of a catalytic amount of [Ir(COD)Cl]2/P(OPh)3 (P/Ir = 1-2) gave a product alkylated at the substituted allylic terminus in 95-99% selectivity. Construction of a quaternary carbon center is possible by this methodology. The reaction of 1,1-dialkyl-2-propenyl acetates gave a product alkylated at the disubstituted allylic terminus exclusively. (E)-2-Alken-1-ol could be successfully used as a substrate. The products alkylated at the substituted allylic terminus were obtained in 93-99% selectivity. A 31P NMR study of the reaction of [Ir(COD)Cl]2 with P(OPh)3 revealed that a catalytically active species is a monophosphite species. The π-acceptor property of P(OPh)3 promotes a carbonium ion character at the substituted allylic terminus and directs the nucleophilic attack to this position. The stereochemistry of the allyl system affected the regioselectivity. In contrast to the reaction of (E)-2-alkenyl acetates, the reaction of (Z)-2-alkenyl acetates gave a product alkylated at the unsubstituted allylic terminus predominantly. This shows that the regioselectivity of the alkylation of the syn π-allyl iridium intermediate is different from that of the anti π-allyl iridium intermediate. (Z)- Selective allylic alkylation of (Z)-2-alkenyl esters is also possible by iridium catalysis.

Palladium-Catalyzed Cross-Coupling of Aryl Halides and Olefinic Epoxides via Palladium Migration

The palladium-catalyzed cross-coupling of aryl halides and olefinic epoxides bearing one to ten carbons between the two functional groups afford good yields of arylated allylic alcohols by a palladium migration process.