10264-56-9Relevant academic research and scientific papers
Zinc(II) Catalysed Conjugate Addition of Grignard Reagents to α,β-Unsaturated Ketones
Jansen, Johan F. G. A.,Feringa, Ben L.
, p. 741 - 742 (1989)
Zinc(II)-diamine complexes are efficient catalysts for the conjugate additions of Grignard reagents to various α,β-unsaturated ketones.
Highly enantioselective cyclization using cationic Rh(I) with chiral ligand
Wu,Funakoshi,Sakai
, p. 6331 - 6334 (1992)
Highly diastereoselective cyclization (> 99% de) of 3R (or S) 3,4-disubstituted 4-pentenals into the corresponding 3,4-cis(or trans)-disubstituted cyclopentanone and highly enantioselective cyclization (> 99% ee) of 4-substituted 4-pentenals into 3-substi
LILY OF THE VALLEY ODORANT
-
Page/Page column 31, (2021/10/22)
The present invention relates to the field of perfumery. More particularly, it relates to a compound of formula (I) as defined herein below, and its uses as perfuming ingredient, to control arthropods or as antimicrobial ingredient. Therefore, following what is mentioned herein, the present invention comprises the invention compound as part of a perfuming composition or of a perfumed consumer product. Moreover, the present invention relates to a properfume compound suitable to release the compound of formula (I).
CuI-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands
Shin, Minkyeong,Gu, Minji,Lim, Sung Soo,Kim, Min-Jae,Lee, JuHyung,Jin, HyeongGyu,Jang, Yun Hee,Jung, Byunghyuck
, p. 3122 - 3130 (2018/07/06)
Catalytic enantioselective conjugate additions of simple alkyl groups to nitroalkenes or cyclic enones that result in the formation of tertiary C–C bonds are described. For these stereoselective addition reactions, new chiral phosphino-oxazoline ligands w
Catalytic enantioselective conjugate addition of Grignard reagents to cyclic enones using C1-1,1′-bisisoquinoline-based chiral ligands
Qi, Gao,Judeh, Zaher M.A.
experimental part, p. 1585 - 1592 (2012/05/04)
New highly constrained chiral C1-1,1′-bisisoquinoline ligands were examined in the enantioselective conjugate addition of Grignard reagents to cyclohexenone and cyclopentenone. The desired 1,4-adducts were obtained in excellent yield and moderate enantiomeric excess (up to 35%). Copyright Taylor & Francis Group, LLC.
Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones
Santos Pisoni, Diego dos,Sobieski da Costa, Jessé,Gamba, Douglas,Petzhold, Cesar Liberato,César de Amorim Borges, Antonio,Ceschi, Marco Antonio,Lunardi, Paula,Saraiva Gon?alves, Carlos Alberto
experimental part, p. 526 - 535 (2010/04/06)
This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3·Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.
Chiral phosphinoazomethinylate salts as new 'one-step available' ligands for copper-catalyzed asymmetric conjugate addition
Wencel, Joanna,Rix, Diane,Jennequin, Thomas,Labat, Stephane,Crevisy, Christophe,Mauduit, Marc
, p. 1804 - 1809 (2008/12/21)
Herein, we report the use of phosphinoazomethinylate salts as chiral efficient ligands for the copper-catalyzed asymmetric conjugate addition (ACA) of dialkylzinc to various enones. These tridentate P,N,O ligands are straightforwardly obtained in a one-step procedure from commercially available enantiopure α-aminoacids. Performing the conjugate addition in the greener AcOEt solvent, high enantioselectivities were reached for both cyclic and acyclic enones ranging between 72% to 98% ee and 96% to >99%, respectively. The 2/1 Cu/ligand ratio required to obtain high enantioselectivities, led us to envisage a copper-copper bi-metallic catalytic system for this transformation.
Highly practical and enantioselective Cu-catalyzed conjugate addition of alkylzinc reagents to cyclic enones at ambient temperature
Krauss, Isaac J.,Leighton, James L.
, p. 3201 - 3203 (2007/10/03)
(Matrix presented) A new ligand for Cu-catalyzed enantioselective additions of dialkylzincs to cyclic enones has been developed. In addition to providing good to excellent enantioselectivities with a range of cyclic enones and dialkylzincs, the ligand has several notworthy features: it can be readily prepared in just two steps, is an air-stable crystalline solid, and provides optimal performance at ambient temperature.
Access to optically pure 4- and 5-substituted lactones: A case of chemical-biocatalytical cooperation
Wang, Shaozhao,Kayser, Margaret M.,Jurkauskas, Valdas
, p. 6222 - 6228 (2007/10/03)
Optically pure or highly enantiomerically enriched 4- and 5-substituted lactones are rather difficult to obtain. Chemical or enzymatic syntheses alone are not particularly successful. A combination of chemical catalysis and biocatalysis, however, provides a convenient route to a variety of these useful chiral compounds. In this paper we describe the synthesis of several optically pure 4- and 5-substituted lactones obtained via whole cell-catalyzed Baeyer-Villiger oxidations of highly enantiomerically enriched 3-alkyl cyclic ketones. Such chiral ketones are readily accessed by recently developed copper-catalyzed asymmetric conjugate reductions of the corresponding enones. A very high proximal regioselectivity and complete chirality transfer was obtained by employing biological Baeyer-Villiger oxidations, using recombinant E. coli strains that overexpress cyclopentanone monooxygenase (CPMO). A comparative study showed that CPMO gives superior results to those obtained with cyclohexanone monooxygenase (CHMO) catalyzed oxidations.
Conjugate reduction of α,β-unsaturated carbonyl compounds catalyzed by a copper carbene complex
Jurkauskas, Valdas,Sadighi, Joseph P.,Buchwald, Stephen L.
, p. 2417 - 2420 (2007/10/03)
(Matrix presented) An N-heterocyclic carbene copper chloride (NHC-CuCl) complex (2) has been prepared and used to catalyze the conjugate reduction of α,β-unsaturated carbonyl compounds. The combination of catalytic amounts of 2 and NaOt-Bu with poly(methy
