163395-33-3

Upstream product

• 1172850-67-7 C₁₇H₂₂O₂ 
• 1823-14-9 5-phenyl-1-pentyne 
• 68-12-2 N,N-dimethyl-formamide 
• 637-59-2 1-Bromo-3-phenylpropane 
• 167482-53-3 1-((tert-Butyldiphenylsilyl)oxy)-6-phenyl-2-hexyne 
• 77877-57-7 6-phenyl-2-hexyn-1-ol 

Downstream Products

• 167482-38-4 6-Phenyl-2-hexyn-1-al diethyl acetal 
• 106575-40-0 7-phenyl-3-heptyn-2-ol 
• 1350626-61-7 3f 
• 1350626-70-8 C₂₂H₃₈OSi 
• 1529754-07-1 (4R)-9-phenylnon-1-en-5-yn-4-ol 
• 1529754-62-8 (3R,4R)-3-methyl-9-phenylnon-1-en-5-yn-4-ol 
• 77877-57-7 6-phenyl-2-hexyn-1-ol 

Relevant academic research and scientific papers

Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes

A copper-catalyzed silylation of propargyl dichlorides was developed to access chloro-substituted allenylsilanes under mild reaction conditions. Moreover, enantioenriched chloro-substituted allenylsilanes can be synthesized in moderate to high yields and good enantioselectivities with this protocol.

Catalytic Anti-Markovnikov Hydroallylation of Terminal and Functionalized Internal Alkynes: Synthesis of Skipped Dienes and Trisubstituted Alkenes

We have developed catalytic anti-Markovnikov hydroallylation of terminal and functionalized internal alkynes. In this article, we describe the development of the reaction, exploration of the substrate scope, and a study of the reaction mechanism. Synthesis of skipped dienes through the hydroallylation of terminal alkyl and aryl alkynes with simple allyl phosphates and 2-substituted allyl phosphates is described. The hydroallylation of functionalized internal alkynes leads to the formation of skipped dienes containing trisubstituted alkenes. We demonstrate that the hydroallylation of internal alkynes can be used in the regio- and diastereoselective synthesis of complex trisubstituted alkenes. A mechanism of the hydroallylation reaction is proposed, and experimental evidence is provided for the key steps of the catalytic cycle. Stoichiometric experiments demonstrate an unexpected role of lithium alkoxide in the carbon-carbon bond-forming step of the reaction. A study of the hydrocupration of internal alkynes provides new insight into the structure, stability, and reactivity of alkenyl copper intermediates, as well as insight into the source of the regioselectivity in reactions of internal alkynes.

Directing group-controlled hydrosilylation: Regioselective functionalization of alkyne

Pt(0)-catalyzed hydrosilylation of unsymmetric alkynes proceeds in a highly regioselective manner with a dimethylvinylsilyl (DMVS) group as the directing group. This hydrosilylation affords a single regioisomer of silylalkenes from propargylic and homopro

Selective oxidation of propargylic alcohols into α,β-acetylenic aldehydes with a TiCl4/Et3N system

A TiCl4/Et3N combination proved to be effective for the selective oxidation of propargylic alcohols into α,β-acetylenic aldehydes in good yields. Treatment of 2-hexyne-1,6-diol with TiCl4/Et3N provided 6-hydroxy-2-hexynal in good yield.

Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

Acetals of α,β-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-β-D-fructopyranose and 1,2-O-isopropylidene-β-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et2Zn and CH2I2 with good diastereoselectivity.The effects of structure of the acetals on enantioselectivity were examined.