113085-39-5Relevant articles and documents
Mild chemo-enzymatic synthesis of polymer-supported cinchona alkaloids and their application in asymmetric Michael addition
Athawale, Vilas,Manjrekar, Narendra
, p. 4541 - 4543 (2001)
Cinchona alkaloid (CA) monomers were synthesised enzymatically in high yield (90%) by selectively acrylating the primary -OH group of the CA, and the co-polymers obtained with acrylonitrile were tested for their efficiency for asymmetric induction in Mich
Enantioselective conjugate addition of thiols to cyclic enones and enals catalyzed by chiral N,N'-dioxide-cadmium iodide complex
Saito, Makoto,Nakajima, Makoto,Hashimoto, Shunichi
, p. 9589 - 9594 (2000)
Chiral N,N'-dioxide-cadmium iodide complex has been shown to catalyze enantioselective conjugate additions of thiols to cyclic enones and enals. The sulfides are generated in high yields and in good enantioselectivities up to 78% ee using 1 mol% of the chiral catalyst. The present reaction provides the first example of utilizing a cadmium complex as a catalyst in enantioselective reaction. (C) 2000 Elsevier Science Ltd.
Enantioselective conjugate addition of thiols to enones and enals catalyzed by chiral N-oxide-cadmium complex
Saito,Nakajima,Hashimoto
, p. 1851 - 1852 (2000)
A novel method of enantioselective conjugate addition of thiols to enones and enals produces sulfides with enantio-selectivities up to 78% ee, employing a cadmium complex of (S)-3,3'-dimethyl-2,2'-biquinoline N,N'-dioxide 1 as a catalyst.
Combined bead polymerization and Cinchona organocatalyst immobilization by thiol-ene addition
Fredriksen, Kim A.,Kristensen, Tor E.,Hansen, Tore
experimental part, p. 1126 - 1133 (2012/09/05)
In this work, we report an unusually concise immobilization of Cinchona organocatalysts using thiol-ene chemistry, in which catalyst immobilization and bead polymerization is combined in a single step. A solution of azo initiator, polyfunctional thiol, polyfunctional alkene and an unmodified Cinchona-derived organocatalyst in a solvent is suspended in water and copolymerized on heating by thiol-ene additions. The resultant spherical and gel-type polymer beads have been evaluated as organocatalysts in catalytic asymmetric transformations.
Highly enantioselective organocatalytic sulfa-michael addition to α, β-unsaturated ketones
Rana, Nirmal K.,Selvakumar, Sermadurai,Singh, Vinod K.
supporting information; experimental part, p. 2089 - 2091 (2010/06/16)
"Chemical Equation Presented" A cinchona alkaloid-derived urea was found to be an efficient organocatalyst for catalyzing enantioselective conjugate addition between thiols and various α,β-unsaturated ketones to provide optically active sulfides with high
Asymmetrie ruthenium-catalyzed 1,4-additions of aryl thiols to enones
Badoiu, Andrei,Bernardinelli, Gerald,Besnard, Celine,Peter Kuendig
supporting information; experimental part, p. 193 - 200 (2010/04/25)
Well defined, stable, one-point binding ruthenium complexes 1 and 2 selectively bind and activate α,β-unsaturated carbonyl compounds for cycloaddition reactions. These mild Lewis acids catalyze asymmetric 1,4-addition reactions of aryl thiols to enones wi
DOSY NMR for monitoring self aggregation of bifunctional organocatalysts: Increasing enantioselectivity with decreasing catalyst concentration
Jang, Hyeong Bin,Rho, Ho Sik,Oh, Joong Suk,Nam, Eun Hye,Park, Sang Eun,Bae, Han Yong,Song, Choong Eui
supporting information; experimental part, p. 3918 - 3922 (2010/09/17)
In this report, we demonstrate that self-aggregation is an intrinsic problem of bifunctional organocatalysts, especially in the case when the substrates do not have functional groups which are able to bind strongly with catalyst. Due to their self-associa
Improved design of inherently chiral calix[4]arenes as organocatalysts
Shirakawa, Seiji,Shimizu, Shoichi
experimental part, p. 1217 - 1222 (2010/08/08)
Improvement of the design of inherently chiral calix[4]arenes as organocatalysts was accomplished via the introduction of a diarylmethanol structure. Novel, inherently chiral calix[4]arenes bearing a tertiary amine or a quaternary ammonium moiety, togethe
Synthesis and resolution of a multifunctional inherently chiral calix[4]arene with an ABCD substitution pattern at the wide rim: The effect of a multifunctional structure in the organocatalyst on enantioselectivity in asymmetric reactions
Shirakawa, Seiji,Kimura, Tomohiro,Murata, Shun-Ichi,Shimizu, Shoichi
experimental part, p. 1288 - 1296 (2009/06/28)
An efficient synthetic route to inherently chiral calix[4]arenes with an ABCD substitution pattern at the wide rim in the cone conformation was developed for the first time. For the synthesis of inherently chiral ABCD-type calix[4]arenes, first 5,11-dibro
Synthesis of an inherently chiral calix[4]arene amino acid and its derivatives: Their application to asymmetric reactions as organocatalysts
Shirakawa, Seiji,Shimizu, Shoichi
experimental part, p. 1916 - 1924 (2009/09/06)
The synthesis of an inherently chiral calix[4]arene amino acid as a chiral building block has been achieved in order for subsequent, transformation to various types of inherently chiral calix[4]arenes. The optically pure, inherently chiral calix[4]arene a