10031-92-2Relevant articles and documents
Copper(i)/phosphine-catalyzed tandem carboxylation/annulation of terminal alkynes under ambient pressure of CO2: One-pot access to 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones
Xie, Jia-Ning,Yu, Bing,Guo, Chun-Xiang,He, Liang-Nian
, p. 4061 - 4067 (2015)
An efficient method for the synthesis of 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones from CO2, terminal alkynes, EtBr, and NHPI (N-hydroxyphthalimide) was developed through a tandem carboxylation/annulation strategy catalyzed by a copper(i)/phosphine system. This one-pot multicomponent reaction was conducted at atmospheric CO2 pressure to afford the target products in good to excellent yields under mild conditions. Notably, a wide range of functional groups were tolerated in this procedure. This protocol with simultaneous formation of four novel bonds i.e. two C-C bonds and two C-O bonds represents an efficient methodology for upgrading CO2 into heterocycles.
Deuteration of α,β-acetylenic esters, amides, or carboxylic acids without using deuterium gas: Synthesis of 2,2,3,3-tetradeuterioesters, amides, or acids
Concellón, José M.,Rodríguez-Solla, Humberto,Concellón, Carmen
, p. 2129 - 2131 (2004)
An easy, simple, rapid, and nonhazardous deuteration of the C-C triple bond of α,β-acetylenic esters, amides, or acids by means of samarium diiodide in the presence of D2O, provides an efficient method for synthesizing 2,2,3,3-tetradeuterioesters, amides, or carboxylic acids, respectively. When H2O is used instead of D2O, saturated carboxylic esters, amides, or acids were isolated. A mechanism to explain these reduction reactions has been proposed.
Total synthesis of a piperidine alkaloid, microcosamine A
Raji Reddy, Chada,Latha, Bellamkonda,Warudikar, Kamalkishor,Singarapu, Kiran Kumar
, p. 251 - 258 (2015)
The first asymmetric total synthesis of a new natural piperidine alkaloid, microcosamine A, has been accomplished from d-serine and d-methyl lactate as chiral pool starting materials. Key features of the strategy include the utility of Horner-Wadsworth-Emmons reaction, Luche reduction, intramolecular carbamate N-alkylation to form the piperidine framework and Julia-Kocienski olefination to install the triene side-chain.
An entry to non-racemic β-tertiary-β-amino alcohols, building blocks for the synthesis of aziridine, piperazine, and morpholine scaffolds
Narczyk, Aleksandra,Stecko, Sebastian
supporting information, p. 5972 - 5981 (2020/08/21)
A method for the preparation of enantiopure β-tert-amino alcohols bearing a tetrasubstituted C-stereocenter, as well as their conversion into selected medicinally privileged heterocyclic systems (morpholines, aziridines, piperazines) is reported. These co
Synthesis of α,β-alkynyl esters and unsymmetrical maleate esters catalyzed by pd/c; An efficient phosphine-free catalytic system for oxidative alkoxycarbonylation of terminal alkynes
Gadge, Sandip T.,Bhanage, Bhalchandra M.
supporting information, p. 981 - 986 (2013/06/27)
Pd/C-catalyzed oxidative alkoxycarbonylation of terminal alkynes using alcohols in the presence of tetrabutylammonium iodide under CO/O2 (5:1 atm) has been investigated. The desired α,β-alkynyl esters and unsymmetrical maleate esters are formed in good to excellent yields under different reaction conditions. The present protocol eliminates the use of phosphine ligands and has straightforward catalyst recovery. The catalyst was recycled up to six times without significant loss of catalytic activity. Georg Thieme Verlag Stuttgart . New York.
Isomerization of electron-poor alkynes to the corresponding (E, E)-1,3-dienes using a bifunctional polymeric catalyst bearing triphenylphosphine and phenol groups
Kwong, Cathy Kar-Wing,Fu, Michael Yunyi,Law, Henry Chun-Hin,Toy, Patrick H.
supporting information; experimental part, p. 2617 - 2620 (2010/11/24)
The use of a bifunctional non-cross-linked polystyrene bearing both phosphine and phenol groups for the organocatalytic isomerization of alkynes bearing electron-withdrawing ester substituents to afford the corresponding (E,E)-dienes in excellent yield an
Halogen chemistry of the red alga Bonnemaisonia
McConnell, Oliver J.,Fenical, William
, p. 233 - 247 (2007/10/10)
Complete accounts of the natural products chemistry of Bonnemaisonia nootkana, B. asparagoides, B. hamifera and Trailliella intricata are described. In contrast to the chemistry of the closely related alga Asparagopsis, Bonnemaisonia spp. do not produce halomethanes, but instead an array of C7-C9 halogen-containing ketones, alcohols and carboxylic acids. Biomimetic syntheses of these compounds suggest they are precursors and products of in vivo Favorsky rearrangements.
