83334-11-6

Upstream product

• 184577-40-0 (+/-)-1-phenylhex-4-yn-3-ol 
• 33046-41-2 6-phenylhex-3-en-2-one 
• 72569-65-4 cis-3,4-epoxy-6-phenyl-1-hexene 
• 72569-65-4 trans-1-phenyl-3,4-epoxyhex-5-ene 

Downstream Products

• 1286679-72-8 (E)-ethyl 3-methyl-7-phenyl-4-heptenoate 
• 60550-53-0 (E)-1-phenyl-3-penten-2-one 

Relevant academic research and scientific papers

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Copper-catalyzed γ-selective and stereospecific allylic alkylation of ketene silyl acetals

Copper-catalyzed allylic alkylation of ketene silyl acetals proceeded with excellent γ-E-selectivity. Efficient α-to-γ chirality transfer with anti-selectivity occurred in the reaction of enantioenriched secondary allylic phosphates, affording enantioenri

Copper-catalyzed γ-selective and stereospecific allyl-aryl coupling between (Z)-acyclic and cyclic allylic phosphates and arylboronates

A Cu-catalyzed allyl-aryl coupling reaction between (Z)-acyclic or cyclic allylic phosphates and arylboronates proceeds with excellent γ-E-selectivity and 1,3-anti chirality transfer, which gives the corresponding coupling products with benzylic and allylic stereogenic centers. The wide availability and easy-to-handle nature of arylboronates, the inexpensiveness of the Cu catalyst system, and the high regio- and stereoselectivities are attractive features of this protocol.

Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers

Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposin

Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols

Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1- butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl.

Formation of cyclopropyl carbinols through a highly diastereoselective hydrozirconation of vinyloxirane derivatives

Cyclopropyl carbinol derivatives were efficiently prepared through a highly diastereoseletive hydrozirconation of vinyloxiranes and the intramolecular attack of the generated alkylzirconocene with the inversion of the configuration at the reacting oxirane carbon.