106470-36-4Relevant academic research and scientific papers
Highly Regio- and Stereoselective Ni-Catalyzed Hydrocyanation of 1,3-Enynes
Sun, Feilong,Ni, Jie,Cheng, Gui-Juan,Fang, Xianjie
supporting information, p. 5956 - 5960 (2020/05/08)
A highly regio- and stereoselective hydrocyanation of 1,3-enynes was implemented by nickel/diphosphine catalysts. A wide range of highly regio- and stereoselective alkenyl nitriles were efficiently prepared. In this transformation, both the tethered alken
Catalytic claisen rearrangement by intercepting ketenimines with propargylic alcohols: A strategy to generate and transform ketenimines from radicals
Yan, Xuyang,Liu, Hongchi,Wei, Shenquan,Huang, Hanmin
supporting information, p. 6794 - 6798 (2020/09/15)
An efficient strategy for facilitating the cross-coupling of two radicals has been established via the coordination of a radical with a metal catalyst. This strategy provides a remarkable ability to harness the reactivity of nitrile-containing azoalkanes and enables a novel cascade reaction with nitrile-containing azoalkanes and propargylic alcohols to be established. By using this reaction, a range of acetylenic and allenic amides were obtained that provides a versatile platform for further derivatizations.
Heteropolyacid-catalyzed direct deoxygenation of propargyl and allyl alcohols
Egi, Masahiro,Kawai, Takuya,Umemura, Megumi,Akai, Shuji
experimental part, p. 7092 - 7097 (2012/10/07)
The combination of H3[PW12O40] ?nH2O (1 mol %) and Et3SiH led to the direct catalytic deoxygenation of propargyl alcohols, in which proper solvent selection Cl(CH2)2Cl vs CF3CH2OH was the key to obtaining better product yields. Under similar conditions, the deoxygenation of allyl alcohols proceeded to give thermodynamically stable alkenes with migration of the double bonds in good yields.
Highly enantioselective addition of linear alkyl alkynes to aromatic aldehydes
Du, Xi,Wang, Qin,He, Xiao,Peng, Rui-Guang,Zhang, Xiao,Yu, Xiao-Qi
experimental part, p. 1142 - 1146 (2011/10/08)
An asymmetric linear alkyl alkyne addition to aromatic aldehydes catalyzed by the Ti-(R)-BINOL system is reported with high enantioselectivity and yield. Our study expands upon the synthetic scope of propargylic alcohols, which could serve as potentially useful intermediates for the synthesis of various natural products.
Chemoselective addition of in situ prepared lithium alkynyl borates to aldehydes: a practical and transition metal free approach toward the synthesis of propargylic alcohols
Francesco, Irene Notar,Renier, Antoine,Wagner, Alain,Colobert, Fran?oise
experimental part, p. 1386 - 1389 (2010/04/25)
A convenient synthesis of functionalized propargylic alcohols arising from the 1,2-addition of lithium alkynyl-trimethyl borate onto aldehydes under transition metal free mild conditions is reported. The reaction tolerates a wide range of functional groups, is highly chemoselective and the propargylic alcohols are isolated in good to excellent yields.
Rhenium-catalyzed 1,3-isomerization of allylic alcohols: Scope and chirality transfer
Morrill, Christie,Beutner, Gregory L.,Grubbs, Robert H.
, p. 7813 - 7825 (2007/10/03)
(Chemical Equation Presented) The scope of the triphenylsilyl perrhennate (O3ReOSiPh3, 1) catalyzed 1,3-isomerization of allylic alcohols has been thoroughly explored. It was found to be effective for a wide variety of secondary and tertiary allylic alcohol substrates bearing aryl, alkyl, and cyano substituents. Two general reaction types were found which gave high levels of product selectivity: those driven by formation of an extended conjugated system and those driven by selective silylation of a particular isomer. The efficiency of chirality transfer with various substrates was investigated, and conditions were found in which secondary and tertiary allylic alcohols could be formed with high levels of enantioselectivity. Consideration of selectivity trends with respect to the nature of the substituents around the allylic system revealed that this is a reliable and predictable method for allylic alcohol synthesis.
A Total Synthesis of the Methyl Ester of the 9,11-Dithia Analogue of 13,14-Dehydro-PGH2
Ghosh, Soumitra S.,Martin, John C.,Fried, Josef
, p. 862 - 876 (2007/10/02)
A total synthesis of the disulfide analogue 2 of 13,14-dehydro-PGH2 methyl ester is described.A key intermediate is the mesylate of the 3-phenyl-2,4-dithiabicyclooctane derivative 37b, which undergoes alkynylation via an episulfonium intermediate t
