23632-41-9Relevant academic research and scientific papers
Asymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co–Catalyzed, Enantioselective Proton-Transfer
Metternich, Jan B.,Reiterer, Martin,Jacobsen, Eric N.
, p. 4092 - 4097 (2020/09/01)
We report an enantioselective Nazarov cyclization catalyzed by chiral hydrogen-bond-donors in concert with silyl Lewis acids. The developed transformation provides access to tri-substituted cyclopentenones in high levels of enantioselectivity (up to 95% e.e.) from a variety of simple unactivated dienones. Kinetic and mechanistic studies are consistent with a reversible 4π-electrocyclization C?C bond-forming step followed by rate- and enantio-determining proton-transfer as the mode of catalysis. (Figure presented.).
Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols
Ji, Enhui,Meng, Haiwen,Zheng, Yue,Ramadoss, Velayudham,Wang, Yahui
supporting information, p. 7367 - 7371 (2019/11/22)
An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).
Process for the Preparation of Idnanones
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Paragraph 0098; 0099, (2019/09/06)
A process of forming compounds of formula I comprising the steps of addition of an amino compound H2NR to a compound of formula (II) followed by cyclization, isomerization and hydrolysis.
Enantioselective Nazarov Cyclizations Catalyzed by an Axial Chiral C6F5-Substituted Boron Lewis Acid
Süsse, Lars,Vogler, Maria,Mewald, Marius,Kemper, Benedict,Irran, Elisabeth,Oestreich, Martin
supporting information, p. 11441 - 11444 (2018/08/28)
A chiral variant of B(C6F5)3 with a 3,3′-disubstituted binaphthyl backbone is shown to catalyze Nazarov cyclizations with high levels of enantio- and diastereocontrol. The parent B(C6F5)3 a
Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds
Chang, Yi-Fan,Jiang, Yi-Rui,Cheng, Wei-Chieh
, p. 543 - 547 (2008/04/13)
The highly efficient and convenient protocol to prepare diverse α,β-unsaturated aldehydes, ketones, and acids via the parallel solid-phase synthesis is developed. The key sulfone linker cleavage strategy is performed by ozonolysis to generate a carbonyl moiety followed by base-mediated polymer-bound sulfinate elimination to release our desired molecules from the resin. All α,β-unsaturated carbonyl compounds are prepared in good purities and yields without further purification.
Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter
Chowdari, Naidu S.,Barbas III, Carlos F.
, p. 867 - 870 (2007/10/03)
(Chemical Equation Presented) A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through L-proline-derived, tetrazole-catalyzed direct asymmetric α-amination
