Thioether–phosphinite and diphosphinite ligands derived from d-xylose for the copper-catalyzed asymmetric 1,4-addition to 2-cyclohexenone

Guimet, Eugeni; Diéguez, Montserrat; Ruiz, Aurora; Claver, Carmen

doi:10.1016/j.tetasy.2005.05.001

Cited by 16 publications

(9 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We could only find one example with D-xylose-derived phosphinite ligands for the asymmetric conjugate addition of organometallic fragments onto enones. 4 Likewise, taddol-or biphenol-based phosphonite ligands have almost exclusively been applied to conjugate additions, 5 but also have been used for the dehydrogenative coupling of hydrosilanes and alcohols. 6 It is important to note that in all examples the active species were generated in situ upon mixing of a copper source and the phosphi(o)nite ligand and that, to the best of our knowledge, no well-defined copper system with these ligands has been applied to catalysis to date.…”

Section: Introductionmentioning

confidence: 99%

Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide–Alkyne Cycloaddition Reactions

et al. 2011

View full text Add to dashboard Cite

The preparation of novel phosphinite- and phosphonite-bearing copper(I) complexes of the general formula [CuX(L)] is reported. These compounds, which remain scarce in the literature, could be prepared using readily available starting materials and were spectroscopically and structurally characterized. These complexes, together with their known phosphine and phosphite analogues, were then applied to the 1,3-dipolar cycloaddition of azides and alkynes, to find that the new complexes displayed the best activities. Full optimization of the reaction conditions resulted in a noteworthy Click catalytic system, active under very mild reaction conditions in the absence of any additive and using low metal loadings.

show abstract

Section: Introductionmentioning

confidence: 99%

Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide–Alkyne Cycloaddition Reactions

et al. 2011

View full text Add to dashboard Cite

show abstract

“…31). 95 Bidentate sugar-phosphite-oxazoline L148 and phosphitephosphoramidite ligands L149 have been screened in the conjugate addition of trimethyl and triethylaluminium to cyclic and acyclic enones. Ee's up to 80% were obtained using L148 which contains encumbered biaryl phosphite moieties and a phenyl oxazoline group (Fig.…”

Section: Miscellaneous Ligandsmentioning

confidence: 99%

Recent advances in enantioselective copper-catalyzed 1,4-addition

et al. 2009

View full text Add to dashboard Cite

A comprehensive overview of recent literature from 2003 concerning advances in enantioselective copper catalysed 1,4-addition of organometallic reagents to alpha,beta-unsaturated compounds is given in this critical review. About 200 ligands and catalysts are presented, with a focus on stereoselectivities, catalyst loading, ligand structure and substrate scope. A major part is devoted to trapping and tandem reactions and a variety of recent synthetic applications are used to illustrate the practicality and current state of the art of 1,4-addition of organometallic reagents. Finally several mechanistic studies are discussed (162 references).

show abstract

“…When ligand 58c was used in the alkylation with AlEt 3 , 48% ee was obtained. 65 In 2005, Khiar and Ferna´ndez et al 66 disclosed a class of thioglycosides-type P,S chiral ligands 60-62 in which 60-61 derived commercially available galactose pentaacetate and 62 was derived from arabinose tetraacetate, respectively. These ligands were examined in Pd-catalyzed asymmetric allylic alkylation and amination, and 60c gave the best results both in alkylation and amination reactions, and proved the anomeric center of sulfur moiety played a significant role in stereocontrol.…”

Section: Ps-type Ligands With Central Chirality and Their Application...mentioning

confidence: 99%

Recent developments on chiral P,S-type ligands and their applications in asymmetric catalysis

2010

View full text Add to dashboard Cite

This feature article illustrates new concepts and approaches for designing new P,S-mixed donor chelating ligands based on three major types of chiral skeleton, the central, axial and planar chirality. The versatility in structural modification is highlighted. It offers an effective pathway to access scientifically useful chiral ligands of diverse electronic and steric properties for optimization in various catalytic enantioselective transformations. In this article, the applications of these optically active ligands in a variety of asymmetric catalytic reactions will be discussed with reference to updated literature findings as well as the author's original research.

show abstract

Thioether–phosphinite and diphosphinite ligands derived from d-xylose for the copper-catalyzed asymmetric 1,4-addition to 2-cyclohexenone

Cited by 16 publications

References 37 publications

Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide–Alkyne Cycloaddition Reactions

Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide–Alkyne Cycloaddition Reactions

Recent advances in enantioselective copper-catalyzed 1,4-addition

Recent developments on chiral P,S-type ligands and their applications in asymmetric catalysis

Contact Info

Product

Resources

About