An investigation of the Lewis acid mediated 1,3-dipolar cycloaddition between N-benzyl-C-(2-pyridyl)nitrone and allylic alcohol. Direct entry to isoxazolidinyl C-nucleosidesElectronic supplementary information (ESI) available: optimized geometries (PDB format). See http://www.rsc.org/suppdata/ob/b3/b304112c/

Merino, Pedro; Tejero, Tomás; Laguna, Mariano; Cerrada, Elena; Moreno, Ana; López, José A.

doi:10.1039/b304112c

Cited by 38 publications

(22 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have shown, in previous reports, that stoichiometric reactions of the N-benzyl-C(2-pyridyl)nitrone with different dipolarophiles in the presence of zinc and silver compounds afforded an increase of both the reaction rate and the selectivity, favouring the formation of one of the possible isomers. The existence of zinc and silver-nitrone complexes during the reaction, which behave as intermediates in the cycloaddition process, was confirmed by different structural techniques [3,4].…”

Section: Introductionmentioning

confidence: 73%

“…Thus, the 1 H NMR spectrum displays a downfield displacement of the nitrone resonances (mainly for d (HC@N) and d (NCH 2 Ph) resonances) as occurred in silver and zinc complexes described previously by us [3,4]. The 19 F NMR spectrum exhibits a characteristic pattern for a square-planar gold(III) complex [6].…”

Section: ) and Angles (°) For [2-pybn-h][aucl 4 ] (5)mentioning

confidence: 83%

“…However, the above mentioned reaction (same reaction conditions as that of analogous zinc and silver complexes [4]) gave no cycloaddition products. Decomposition to metallic gold as a consequence of reduction from gold(III) and gold(I) to gold(0) was observed instead in all cases.…”

Section: ) and Angles (°) For [2-pybn-h][aucl 4 ] (5)mentioning

confidence: 85%

“…In order to determine the possible intermediates of the cycloaddition reaction, as confirmed in the case of zinc and silver derivatives, [4] we performed the reaction between the nitrone 1 and some of the organometallic gold(III) and gold(I) complexes (Scheme 1).…”

Section: ) and Angles (°) For [2-pybn-h][aucl 4 ] (5)mentioning

confidence: 99%

“…It is noteworthy that some of these reactions [2a] can be also catalyzed by silver salts but with much lower yields. Our research group has recently studied the 1,3-dipolar cycloaddition between nitrones and alkenes mediated by Lewis acids [3,4]. Despite the extensive study performed in this field by several laboratories [5] there are not that many examples in which a metallic complex with a nitrone as ligand catalyzes the dipolar cycloaddition.…”

Section: Introductionmentioning

confidence: 98%

See 4 more Smart Citations

Organometallic gold(III) and gold(I) complexes as catalysts for the 1,3-dipolar cycloaddition to nitrones: synthesis of novel gold–nitrone derivatives

Adé

Cerrada

Contel

et al. 2004

Journal of Organometallic Chemistry

Self Cite

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 73%

Section: ) and Angles (°) For [2-pybn-h][aucl 4 ] (5)mentioning

confidence: 83%

Section: ) and Angles (°) For [2-pybn-h][aucl 4 ] (5)mentioning

confidence: 85%

Section: ) and Angles (°) For [2-pybn-h][aucl 4 ] (5)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

See 3 more Smart Citations

Organometallic gold(III) and gold(I) complexes as catalysts for the 1,3-dipolar cycloaddition to nitrones: synthesis of novel gold–nitrone derivatives

Adé

Cerrada

Contel

et al. 2004

Journal of Organometallic Chemistry

Self Cite

View full text Add to dashboard Cite

Zinc Trifluoromethanesulfonate

Ham¹,

Deng²,

Selvakumar³

et al. 2011

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Silver: Inorganic & Coordination ChemistryBased in part on the article Silver: Inorganic & Coordination Chemistry by W. Ewen Smith which appeared in the Encyclopedia of Inorganic Chemistry, First Edition .

Mak

Zhao

2005

Encyclopedia of Inorganic Chemistry

View full text Add to dashboard Cite

The present review is a complete rewrite of the original article in the first edition. The new version provides concise and up‐to‐date information on the inorganic and coordination compounds of silver in oxidation states ranging from subvalent to Ag(IV). Literature coverage is extended to October 2004, and pertinent references are listed for the convenience of the interested reader. The presentation is organized under the following headings: 1. Introduction; 2. Subvalent silver compounds; 3. Silver(I) compounds (under subheadings: 3.1 Halides and pseudohalides; 3.2 Phosphorus donor ligands; 3.3 Nitrogen donor ligands; 3.4 Oxygen donor ligands; 3.5 Chalcogen donor ligands; 3.6 Silver‐rich compounds); 4. Silver(II) compounds; 5. Silver(III) and silver(IV) compounds; 6. Catalysis. The structural features of the compounds are described, and specific examples are illustrated with five figures. For the most important +1 oxidation state of silver, particular emphasis is placed on recent highlights and advances in new areas such as double and multiple salts of silver, silver(I) polyhedra with encapsulated acetylenediide (C 2 2− ) species (symbolized as C 2 @Ag n ), argentophilic Ag(I)⋯Ag(I) interaction in supramolecular assembly, halide‐centered Ag n cages, mixed‐metal clusters, and silver‐rich chalcogenide supercluster complexes. Modern application of inorganic silver catalysts, of both achiral and chiral types, to organic synthesis is presented with selected examples from the recent literature.

show abstract

Cited by 38 publications

References 49 publications

Organometallic gold(III) and gold(I) complexes as catalysts for the 1,3-dipolar cycloaddition to nitrones: synthesis of novel gold–nitrone derivatives

Organometallic gold(III) and gold(I) complexes as catalysts for the 1,3-dipolar cycloaddition to nitrones: synthesis of novel gold–nitrone derivatives

Zinc Trifluoromethanesulfonate

Silver: Inorganic & Coordination ChemistryBased in part on the article Silver: Inorganic & Coordination Chemistry by W. Ewen Smith which appeared in the Encyclopedia of Inorganic Chemistry, First Edition .

Contact Info

Product

Resources

About