18215-71-9Relevant articles and documents
Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu?H-Catalyzed Si?O Coupling
Seliger, Jan,Dong, Xichang,Oestreich, Martin
supporting information, p. 1970 - 1974 (2019/01/29)
A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst-controlled enantioselective silylation. This non-enzymatic kinetic resolution is catalyzed by a Cu?H species and makes use of the commercially available precatalyst MesCu/(R,R)-Ph-BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl- as well as dialkyl-substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post-functionalization in this position (s up to 207).
Synthesis of 4-Oxoisoxazoline N-Oxides via Pd-Catalyzed Cyclization of Propargylic Alcohols with tert-Butyl Nitrite
Feng, Kai-Wen,Ban, Yong-Liang,Yuan, Pan-Feng,Lei, Wen-Long,Liu, Qiang,Fang, Ran
supporting information, p. 3131 - 3135 (2019/05/10)
A cyclization of propargylic alcohols with tert-butyl nitrite at room temperature in air was achieved using Pd(OAc)2 as catalyst. The first reported 4-oxoisoxazoline N-oxides could be directly accessed from a range of multisubstituted propargylic alcohols in moderate to excellent yields under mild conditions. Density functional theory calculations indicated that the reaction proceeds through a palladium-catalyzed NO2 addition that efficiently generates a ketoxime radical, which eventually produces 4-oxoisoxazoline N-oxide.
Alkynylaluminum Synthesis Catalyzed by a Zwitterionic Neodymium(III) Heterobimetallic Compound
Kanbur, Uddhav,Ellern, Arkady,Sadow, Aaron D.
, p. 4409 - 4414 (2019/01/03)
The reaction of H{PhB(OxMe2)2C5H5} (OxMe2 = 4,4-dimethyl-2-oxazoline) with Nd(AlMe4)3 (1) provides Me2Al{(OxMe2)2PhBCp}Nd(AlMe4)2
SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
Martins, Guilherme M.,Back, Davi F.,Kaufman, Teodoro S.,Silveira, Claudio C.
, p. 3252 - 3264 (2018/03/25)
A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,
Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
supporting information, p. 5353 - 5356 (2018/09/13)
An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
Gold-Catalyzed Rearrangement of Alkynyl Donor-Acceptor Cyclopropanes to Construct Highly Functionalized Alkylidenecyclopentenes
Chen, Huiyu,Zhang, Jing,Wang, David Zhigang
supporting information, p. 2098 - 2101 (2015/05/13)
A gold-catalyzed 1,7-addition-cyclization-elimination cascade sequence performed on a range of alkynyl-substituted donor-acceptor-type cyclopropanes provides facile entry to highly functionalized exo-alkylidenecyclopentenes under very mild conditions. Iso
Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with allylB(pin)
Le, Hai,Batten, Amanda,Morken, James P.
supporting information, p. 2096 - 2099 (2014/05/06)
Application of internal electrophiles in catalytic stereospecific allyl-allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation ca
Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations
Zhang, Huan,Tanimoto, Hiroki,Morimoto, Tsumoru,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi
supporting information, p. 5222 - 5225 (2013/11/06)
Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.
Domino gold-catalyzed rearrangement and fluorination of propargyl acetates
De Haro, Teresa,Nevado, Cristina
supporting information; experimental part, p. 248 - 249 (2011/02/23)
A combination of IPrAuNTf2 as catalyst in the presence of Selectfluor has been successfully used for the high yielding synthesis of α-fluoroenones via 1,3-acyloxy rearrangement of propargyl acetates followed by Csp2-F bond formation,
A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature
Pennell, Matthew N.,Unthank, Matthew G.,Turner, Peter,Sheppard, Tom D.
supporting information; experimental part, p. 1479 - 1482 (2011/04/26)
Meyer-Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1-2 mol % PPh3AuNTf2, in the presence of 0.2 equiv of 4-methoxyphenylboronic acid or 1 equiv of methanol. Good to excellent yields of enones can be obtained from secondary and tertiary alcohols, with high selectivity for the E-alkene in most cases. A one-pot procedure for the conversion of primary propargylic alcohols into β-arylketones was also developed, via Meyer-Schuster rearrangement followed by Pd-catalayzed addition of a boronic acid.(Figure Presented)
