68099-19-4Relevant academic research and scientific papers
Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji-Trost of Benzotriazoles with 1,3-Dienes
Li, Yin-Lin,Wu, Hai-Hong,Zhang, Junliang,Zhang, Pei-Chao
supporting information, p. 13010 - 13015 (2021/09/07)
The asymmetric denitrogenative cycloaddition has emerged as a powerful tool to build chiral aza-heterocyles. However, only one example of asymmetric denitrogenative cycloaddition of benzotriazole with unsaturated hydrocarbons has been explored so far, bec
An elusive thermal [2 + 2] cycloaddition driven by visible light photocatalysis: Tapping into strain to access C 2-symmetric tricyclic rings
Singh, Kamaljeet,Trinh, Winston,Weaver, Jimmie D.
supporting information, p. 1854 - 1861 (2019/02/20)
A mild and operationally simple methodology is reported for the synthesis of cyclobutane rings imbedded within a C2-symmetric tricyclic framework. The method uses visible light and an iridium-based photocatalyst to drive the oft-stated "forbidden" thermal
Preparation of optically active cycloalkenes bearing all-carbon quaternary stereogenic centres: Via lipase-oxovanadium combo-catalysed dynamic kinetic resolution
Kawanishi, Shinji,Sugiyama, Koji,Oki, Yasuhiro,Ikawa, Takashi,Akai, Shuji
supporting information, p. 411 - 417 (2017/08/14)
In this study, a novel asymmetric synthesis of all-carbon quaternary stereogenic centres is developed by the connection of three prochiral or achiral components - conjugated enones, organometallic compounds and vinyl esters - at the C-1 position of the enones. This method involves three sequential steps: 1,2-nucleophilic addition of an organometallic compound to the enone, lipase-catalysed dynamic kinetic resolution (DKR) of the tert-allylic alcohol and the Ireland-Claisen rearrangement of the optically active allyl ester thus generated. This method features the effective use of acyl moieties installed by DKR for achieving high atom economy. The application of this method to the protective-group-free asymmetric total synthesis of (-)-crinane, a core structure of a class of natural alkaloids, has demonstrated that it can alter a known synthetic pathway of a racemate into an asymmetric synthesis of an optically pure molecule while reducing the total transformation steps and increasing the overall yield. With these advantages, this method is practical and attractive as a new environmentally benign protocol.
Migratory dynamic kinetic resolution of carbocyclic allylic alcohols
Manzuna Sapu, Chicco,G?rbe, Tams,Lihammar, Richard,B?ckvall, Jan-E.,Deska, Jan
supporting information, p. 5952 - 5955 (2015/02/19)
A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Bronsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity
Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent
Li, Jingjie,Tan, Ceheng,Gong, Jianxian,Yang, Zhen
supporting information, p. 5370 - 5373 (2015/01/09)
A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).
Pt-catalyzed oxidative rearrangement of cyclic tertiary allylic alcohols to enones using aqueous hydrogen peroxide
Nagamine, Takashi,Kon, Yoshihiro,Sato, Kazuhiko
supporting information; experimental part, p. 744 - 746 (2012/09/22)
An oxidative rearrangement of cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by Pt black catalyst with aqueous hydrogen peroxide is described. The reaction proceeds under organic solvent- and halide-free conditions and gives only water as a coproduct. The Pt black catalyst is commercially available and can be reused at least four times.
Chiral phosphine-phosphite ligands in the enantioselective 1,4-addition of Grignard reagents to α,β-unsaturated carbonyl compounds
Naeemi, Qaseem,Robert, Tobias,Kranz, Darius P.,Velder, Janna,Schmalz, Hans-Guenther
experimental part, p. 887 - 892 (2011/08/22)
A library of chiral phosphine-phosphite ligands was evaluated in the Cu-catalyzed asymmetric 1,4-addition of Grignard reagents to cyclopentenone, cycloheptenone and 5,6-dihydro-2H-pyran-2-one. TADDOL-based ligands 1a and 1b with a bulky substituent at the
Syntheses of trans -SCH-A and cis -SCH-A via a stereodivergent cyclopropanation protocol
Csatayova, Kristina,Davies, Stephen G.,Lee, James A.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
supporting information; experimental part, p. 3152 - 3155 (2010/09/05)
(Figure Presented) A highly diastereoselective cyclopropanation protocol has been employed in the syntheses of trans-SCH-A and cis-SCH-A. This strategy encompasses a stereodivergent procedure for the preparation of syn- and anti-cyclopropane diastereoisom
Boronic acid catalyzed Friedel-Crafts reactions of allylic alcohols with electron-rich arenes and heteroarenes
McCubbin, J. Adam,Hosseini, Hamidreza,Krokhin, Oleg V.
supporting information; experimental part, p. 959 - 962 (2010/04/30)
(Chemical Equation Presented) Pentafluorophenylboronic acid catalyzes the regioselective coupling of structurally diverse allylic alcohols with a variety of electron-rich aromatic and heteroaromatic substrates under ambient conditions. The commercially av
Oxidative rearrangement of tertiary allylic alcohols employing oxoammonium salts
Shibuya, Masatoshi,Tomizawa, Masaki,Iwabuchi, Yoshiharu
, p. 4750 - 4752 (2008/09/20)
(Chemical Equation Presented) Practical and highly efficient methods for oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds employing oxoammonium salts are described. The methods developed are applicable to acyclic substrates as well as medium membered ring substrates and macrocyclic substrates. The counteranion of the oxoammonium salt plays crucial roles on this oxidative rearrangement.
