27907-00-2Relevant academic research and scientific papers
The shortest (four-step) total synthesis of the eight-membered cyclic ether (rac)- and (-)-cis-lauthisan
Hernandez-Torres, Gloria,Mateo, Julio,Urbano, Antonio,Carreno, M. Carmen
, p. 6259 - 6262 (2013)
Access to the eight-membered cyclic ether (rac)- and (-)-cis-lauthisan was achieved in two complementary ways in only four steps for the longest linear sequence by starting from commercially available materials. The sequence features a cis-stereoselective reductive cyclization as the key step. Copyright
Studies on K2CO3-Catalyzed 1,4-Addition of 1,2-Allenic Ketones with Diethyl Malonate: Controlled Selective Synthesis of β,γ-Unsaturated Enones and α-Pyrones
Ma, Shengming,Yu, Shichao,Yin, Shaohu
, p. 8996 - 9002 (2003)
The K2CO3 (10 mol%)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized β,γ-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-alle
Mechanism-Based Approach to Reagent Selection for Oxidative Carbon?Hydrogen Bond Cleavage Reactions
Miller, Jenna L.,Zhou, Lin,Liu, Peng,Floreancig, Paul E.
supporting information, (2021/12/09)
Numerous hydride-abstracting agents generate the same cationic intermediate, but substrate features such as intermediate cation stability, oxidation potential, and steric environment can influence reaction rates in an oxidant-dependent manner. This manusc
Synthesis of vinylic sulfones in aqueous media
Goh, Jeffrey,Maraswami, Manikantha,Loh, Teck-Peng
supporting information, p. 1060 - 1065 (2021/02/16)
A green method for the sulfination of allenic carbonyl compounds to access a wide variety of vinylic sulfones is developed. This reaction works in aqueous media under very mild conditions. This reaction is atom economic. A wide variety of vinylic sulfones could be obtained in moderate to excellent yields with wide functional group tolerance. The efficiency of this method is demonstrated in some reactions where the desired products can be isolated by filtration.
One-pot, regioselective synthesis of homopropargyl alcohols using pro-pargyl bromide and carbonyl compound by the mg-mediated reaction under solvent-free conditions
Devaramani, Samrat,Li, Shunxi,Ma, Xiaofang,Xu, Daqian,Zhao, Guohu
supporting information, p. 438 - 442 (2020/04/21)
The elimination of volatile organic solvents in organic synthesis is the most important goal in “Green” chemistry. We report a simple, efficient and facile method for the addition of progargyl bromide to carbonyl compounds using Mg metal as a mediator under solvent-free conditions which could regioselectively generate homopropargyl alcohols efficiently in good to excellent yields. The procedure has advantages such as short reaction time, operationally simple, excellent product yields, high regioselectivity and organic solvent-free.
Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation
Andrade, Silvia R. C. P.,Freitas, Jucleiton J. R.,Freitas, Juliano C. R.,Freitas, Queila P. S. B.,Menezes, Paulo H.,Oliveira, Roberta A.
supporting information, p. 168 - 174 (2020/03/27)
The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.
Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl3
López-Martínez, Josefa L.,Torres-García, Irene,Rodríguez-García, Ignacio,Mu?oz-Dorado, Manuel,álvarez-Corral, Miriam
, p. 806 - 816 (2019/01/24)
CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis of natural products.
Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives
Sherwood, Alexander M.,Williamson, Samuel E.,Johnson, Stephanie N.,Yilmaz, Anil,Day, Victor W.,Prisinzano, Thomas E.
, p. 980 - 992 (2018/01/27)
A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated
C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation
Liang, Tao,Woo, Sang Kook,Krische, Michael J.
supporting information, p. 9207 - 9211 (2016/08/05)
The canonical SN2 behavior displayed by alcohols and activated alkyl halides in basic media (O-alkylation) is superseded by a pathway leading to carbinol C-alkylation under the conditions of rhodium-catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described.
Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil
Freitas, Jucleiton J.R.,Couto, Tulio R.,Cavalcanti, Italo H.,Freitas, Juliano C.R.,Barbosa, Queila P.S.,Oliveira, Roberta A.
supporting information, p. 760 - 765 (2016/02/05)
The propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil, an inexpensive and readily available clay, in a chemo- and regioselective way is described. The method is simple and avoids the use of air and moisture sensitive organometallics and products were obtained in good to moderate yields.
