72206-40-7Relevant academic research and scientific papers
Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes
Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong
supporting information, p. 6041 - 6045 (2021/08/03)
Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
Kinetic Resolution of Propargylic Ethers via [2,3]-Wittig Rearrangement to Synthesize Chiral α-Hydroxyallenes
Xu, Xi,Dong, Shunxi,Feng, Lili,Wang, Sijing,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 2692 - 2696 (2020/03/30)
An efficient kinetic resolution of propargyloxy dicarbonyl compounds via asymmetric [2,3]-Wittig rearrangement was achieved by using a chiral N,N′-dioxide/NiII complex catalyst. Various chiral α-allenyl alcohols were obtained in high enantioselectivities under mild conditions. The utility of this method was readily demonstrated in the asymmetric synthesis of the chiral 2,5-dihydrofuran derivative.
Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters
Ni, Ke,Meng, Ling-Guo,Ruan, Hongjie,Wang, Lei
supporting information, p. 8438 - 8441 (2019/07/22)
The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.
1,8-Diazabicyclo[5.4.0]undec-7-ene-Catalyzed Carbonylative Cyclization of Propargylic Alcohols with Elemental Sulfur
Hu, Yuya,Yin, Zhiping,Werner, Thomas,Spannenberg, Anke,Wu, Xiao-Feng
, p. 1274 - 1276 (2018/03/21)
A carbonylation procedure involving the cyclization of propargylic alcohols with elemental sulfur was developed. With 1,8-diazabicyclo[5.4.0]undec-7-ene as the catalyst, elemental sulfur and carbon monoxide are activated and incorporated into propargylic
Regio- and stereo-selective intermolecular [2+2] cycloaddition of allenol esters with C60 leading to alkylidenecyclobutane-annulated fullerenes
Ueda, Mitsuhiro,Sakaguchi, Tsukasa,Hayama, Miho,Nakagawa, Takafumi,Matsuo, Yutaka,Munechika, Aiko,Yoshida, Shunsuke,Yasuda, Hiroshi,Ryu, Ilhyong
supporting information, p. 13175 - 13178 (2016/11/09)
The intermolecular [2+2] cycloaddition of allenol esters, which were in situ generated by Pt-catalyzed 1,3-acyloxy migration of propargylic esters, with C60 proceeded regio- and stereo-selectively to give a novel class of alkylidenecyclobutane-annulated fullerenes. The cyclobutane-annulated fullerene derivatives have high-lying LUMO levels, which gave a high open-circuit voltage in organic solar cell applications. The observed high electron mobility provided a good fill factor compared with the PCBM-based devices.
Gold-catalyzed oxidative reactions of propargylic carbonates involving 1,2-carbonate migration: Stereoselective synthesis of functionalized alkenes
Sun, Ning,Chen, Ming,Liu, Yuanhong
, p. 4055 - 4067 (2014/05/20)
A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant has been developed. The reaction provides efficient access to α-functionalized-α,β-unsaturated ketones with excellent regio- and diastereoc
Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines
Saravanan, Thangavelu,Jana, Sushital,Chadha, Anju
supporting information, p. 4682 - 4690 (2014/06/24)
Various aryl and alkyl substituted optically pure propargyl alcohols were obtained with excellent ee (up to >99%) and isolated yields (up to 87%) by deracemization using whole cells of Candida parapsilosis ATCC 7330. The whole cells show substrate specificity towards alkyl substituted propargyl alcohols and a switch in the enantioselectivity has been observed from 'R' to 'S' upon increasing the chain length. For the first time, enantiopure (R)-4-(3-hydroxybut-1-ynyl)benzonitrile, (R)-4-(biphenyl-4-yl)but-3-yn-2-ol, (S)-ethyl 3-hydroxy-5-phenylpent-4-ynoate and (S)-4-phenylbut-3-yne-1,2-diol were obtained using this strategy. Optically pure propargyl alcohol thus obtained was used as a chiral starting material in the synthesis of enantiomerically enriched poly-substituted pyrrolidines and a pyrrole derivative successfully demonstrating a chemoenzymatic route. This journal is
Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition
Chen, Wei,Tay, Jia-Hui,Ying, Jun,Yu, Xiao-Qi,Pu, Lin
, p. 2256 - 2265 (2013/04/24)
The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.
Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions
Ting, Chun-Ming,Hsu, Yi-Ling,Liu, Rai-Shung
supporting information; experimental part, p. 6577 - 6579 (2012/07/31)
We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.
Solvent-free synthesis of propargylic alcohols using zno as a new and reusable catalyst by direct addition of alkynes to aldehydes
Hosseini-Sarvari, Mona,Mardaneh, Zahra
experimental part, p. 4297 - 4303 (2012/02/16)
Under solvent-free conditions, the synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes promoted by ZnO as a novel, commercially, and cheap catalyst is described. Furthermore, the catalyst can be reused for several times w
