139313-56-7Relevant articles and documents
Highly enantioselective addition of phenylethynylzinc to aldehydes catalyzed by chiral cyclopropane-based amino alcohols
Zheng, Bing,Li, Zhiyuan,Liu, Feipeng,Wu, Yanhua,Shen, Junjian,Bian, Qinghua,Hou, Shicong,Wang, Ming
, p. 15422 - 15433 (2013)
The enantioselective addition of phenylethynylzinc to aldehydes catalyzed by a series of cyclopropane-based amino alcohol ligands 7 was investigated. The reactions afforded chiral propargylic alcohols in high yields (up to 96%) and with excellent enantios
Effective activation of chiral BINOL/Ti(OiPr)4 catalyst with phenolic additives for the enantioselective alkynylation of aldehydes
Lu, Gui,Li, Xingshu,Chen, Gang,Chan, Wing Lai,Chan, Albert S. C.
, p. 449 - 452 (2003)
The activation of chiral titanium(IV) complexes with achiral activators, e.g. phenol, is found to provide higher levels of enantioselectivity than those attained with an enantiopure catalyst in the alkynylations of both aromatic and aliphatic aldehydes.
A boron-oxygen transborylation strategy for a catalytic midland reduction
Nicholson, Kieran,Dunne, Joanne,DaBell, Peter,Garcia, Alexander Beaton,Bage, Andrew D.,Docherty, Jamie H.,Hunt, Thomas A.,Langer, Thomas,Thomas, Stephen P.
, p. 2034 - 2040 (2021/02/20)
The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transb
Ti-catalyzed regioselective ring-opening alkynylation of epoxides with haloalkynes
Zhang, Di,Li, Hao,Yi, Dong,Tu, Shijing,Qi, Zhongyu,Wei, Siping,Fu, Qiang,Fu, Haiyan,Du, Xi
supporting information, (2021/11/01)
Ti-catalyzed ring-opening alkynylation of epoxides with haloalkynes has been achieved, allowing an efficient and regioselective entry to various propargylic alcohols in moderate to good yields. The developed protocol features extremely mild reaction conditions, broad substrate scope, varied functional group compatibility, and chemospecificity in the rearrangements of epoxides to aldehydes.
Green and efficient synthesis method of chiral alkynol
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Paragraph 0038-0040, (2020/02/14)
The invention relates to a method for preparing alkynol in the technical field of chemical engineering, which is characterized in that in ethanol and formate, under the catalysis of an iridium catalyst of a chiral spiro pyridylaminophosphine ligand, acety
Formation of β-Oxo- N-vinylimidates via Intermolecular Ester Incorporation in Huisgen Cyclization/Carbene Cascade Reactions
Wang, Qinxuan,May, Jeremy A.
supporting information, p. 9579 - 9584 (2021/01/09)
Unusual intermolecular trapping of esters by carbenes generated via a Huisgen cyclization/retroelectrocyclization/dediazotization cascade reaction is presented. β-Oxo-N-vinylimidates could be obtained in one step from propargyl carbonazidates. Mechanistic control experiments suggested reversible dipole formation by ester addition to the carbene, and nitrogen attack to the ester carbonyl was irreversibly followed by stereoselective decarboxylative elimination to give the Z-vinyl imidate. The cross-conjugated enone, imidate, and enamine functional groups in the β-oxo-N-vinylimidates offer novel syntheses of functionalized oxazoles.
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.
DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives
De, Rimpa,Savarimuthu, Antony,Ballav, Tamal,Singh, Pijush,Nanda, Jayanta,Hasija, Avantika,Chopra, Deepak,Bera, Mrinal K.
supporting information, p. 1587 - 1592 (2020/08/28)
A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.
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.
Gold-catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso-Povarov Reactions
Chen, Ching-Nung,Liu, Rai-Shung
supporting information, p. 9831 - 9835 (2019/07/04)
This work reports the first success of the nitroso-Povarov reaction, involving gold-catalyzed [4+2] annulations of nitrsoarenes with substituted cyclopentadienes. In this catalytic sequence, nitrosoarenes presumably attack gold-π-dienes by a 1,4-addition pathway, generating allylgold nitrosonium intermediates to complete an intramolecular cyclization. Acyclic dienes are also applicable substrates, and affording oxidative nitroso-Povarov products.
