A novel C1-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(-)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)2H2O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%-76% range.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272271 | PMC |
| http://dx.doi.org/10.3390/molecules20046224 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Rhodium(I)-Catalyzed Highly Enantioselective Insertion of Carbenoid into Si-H: Efficient Access to Functional Chiral Silanes.
J Am Chem Soc
February 2016
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
The first rhodium(I)-catalyzed enantioselective Si-H insertion reaction of α-diazoesters and α-diazophosphonates has been developed. The use of a C1-symmetric chiral diene ligand enabled the asymmetric reaction to proceed under exceptionally mild conditions and give versatile chiral α-silyl esters and phosphonates with excellent enantioselectivities (up to 99% ee). The mechanism and stereochemical pathway of this novel Rh(I)-carbene-directed Si-H insertion was investigated by deuterium kinetic isotope effect experiments and DFT calculations.
View Article and Find Full Text PDFCu (II)-catalyzed asymmetric henry reaction with a novel C1-symmetric aminopinane-derived ligand.
Molecules
April 2015
Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway.
A novel C1-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(-)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)2H2O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%-76% range.
View Article and Find Full Text PDFComplementary catalytic strategies to access alpha-chiral aldehydes.
Chimia (Aarau)
January 2014
Department of Organic Chemistry, University of Geneva, Geneva.
The present article summarizes the development of two novel and complementary catalytic methods to access alpha-chiral aldehydes. A C1-symmetric chiral (P,N) ligand with a structure derived from the ubiquitous binepine scaffold has been specifically designed for the Pd-catalyzed alpha-arylation of aldehydes to access indane derivatives with a well-defined quaternary stereocenter in high yields and excellent enantioselectivities. In addition, a dinuclear palladium hydride catalyst has been synthesized for the isomerization of terminal and trisubstituted epoxides into aldehydes and ketones respectively.
View Article and Find Full Text PDFThe coordination chemistry of the C1-symmetric bis(silyl)methyl ligand [CH(SiMe3){SiMe(OMe)2}]- revisited: Li/M- (M = Zn, Tl, Ce), Li4- or Ce2-methoxy-bridged alkyls.
Dalton Trans
September 2005
Chemistry Department, University of Sussex, Brighton, UKBN1 9QJ.
The following crystalline oligonuclear metal alkyls have been synthesised under mild conditions and structurally characterised: [(THF)Li(mu-A)(mu-Cl)(mu3-OMe)Zn]2, [Li(mu-A)2Tl]2(4 and 4'), [Li4(mu-A)3(micro3-OMe)]5, [(mu-A)Li2(mu-A)2(mu3-OMe)Ce(A)](6) and [Ce(A)(mu2-OMe){mu2-OS(O)(CF3)O}]2(11)[= CH(SiMe3){SiMe(OMe)2}]. Compounds 2-6 were obtained from [Li(mu-A)]infinity(1) and ZnCl2(3), TlCl (4 and 4' and 5) and CeCl3(6), and 11 was isolated from K(A)(prepared from 1 + KOBu(t)) and cerium(III) triflate Ce(OTf)3. The principal novel features are (i) and (ii) as follows.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!