Asymmetric Diels-Alder reaction between acrylates and cyclopentadiene in the presence of chiral catalysts

Mamedov, E. G.

doi:10.1134/s1070427206100120

Cited by 3 publications

(2 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Titanium complexes were subsequently replaced by aluminum Lewis acid catalysts. Koga’s catalyst ( 55 ) along with a series of aluminum complexes ( 56 – 58 ) based on Kagan’s catalyst , were studied. After optimization of the reaction conditions, the synthesis of (+)-( 1 ) was achieved in moderate yields of 45%.…”

Section: Structural Attributes and Synthesis Of Vince Lactammentioning

confidence: 99%

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

2012

View full text Add to dashboard Cite

| Chem. Rev. 2012, 112, 4642−4686 4.4.3. Enantioselective Synthesis of Various Heterocyclic Compounds via ROM-RCM Domino Metathesis of Ring-Opened Vince Lactam Derivatives 4669 4.5. Use of Vince Lactam as a Standard in Chemical Analysis of Compounds and Optical Activity of Stereoisomers 4669 5. Conclusions 4669 Author Information 4669 Corresponding Author 4669 Notes 4669 Biographies 4670 Acknowledgments 4670 Abbreviations 4670 References 4671V). The well-known preference of the hydrolase enzymes to attack a substrate from si face rather than re face was studied in the system via molecular modeling of the two tetrahedral intermediates. These studies revealed that the complexes modeled on re face for both the isomers of the racemate were highly unfavorable. Furthermore, the unpropitious steric Scheme 12. Biocatalytic Resolution of Vince Lactam Followed by Various Chemical Transformations to Obtain the Desired Stereoisomers of Synthetic Intermediates Scheme 13. Proposed Mechanistic Pathway for the Biocatalytic Hydrolysis of Vince Lactam Chemical Reviews Review dx.

show abstract

Section: Structural Attributes and Synthesis Of Vince Lactammentioning

confidence: 99%

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

2012

View full text Add to dashboard Cite

show abstract

“…The acid catalyzed Diels-Alder reactions, namely between cyclopentadiene (CPD) and acrylates, is well documented, [1,[3][4][5][6][7][8][9][10][11][12][13][14][15] the most important used Lewis acids being Al(III), Fe(III) or boron complexes. The use of such strong acids is needed because ester dienophiles (as acrylate ones) are not very reactive.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of L-serine derivative ligands in Diels-Alder reaction between cyclopentadiene and methyl acrylate

Sousa

Freire

Rodríguez‐Borges³

2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

New L-serine derivative ligands were prepared and tested as co-catalyst in the Diels-Alder reactions between cyclopentadiene (CPD) and methyl acrylate in the presence of several Lewis acids. The catalytic potential of the in situ formed complexes was evaluated based on the reaction yield. Bidentate serine ligands showed good ability to coordinate medium strength Lewis acids, thus boosting their catalytic activity. The synthesis of the L-serine ligands proved to be highly efficient and straightforward. Silylated serines were also prepared for posterior grafting onto inorganic materials for application in heterogeneous catalysis.

show abstract

New L-Serine Derivative Ligands as Cocatalysts for Diels-Alder Reaction

Sousa

Rodríguez‐Borges

Freire

2013

ISRN Organic Chemistry

View full text Add to dashboard Cite

New L-serine derivative ligands were prepared and tested as cocatalyst in the Diels-Alder reactions between cyclopentadiene (CPD) and methyl acrylate, in the presence of several Lewis acids. The catalytic potential of the in situ formed complexes was evaluated based on the reaction yield. Bidentate serine ligands showed good ability to coordinate medium strength Lewis acids, thus boosting their catalytic activity. The synthesis of the L-serine ligands proved to be highly efficient and straightforward.

show abstract

Asymmetric Diels-Alder reaction between acrylates and cyclopentadiene in the presence of chiral catalysts

Cited by 3 publications

References 7 publications

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics

Synthesis and application of L-serine derivative ligands in Diels-Alder reaction between cyclopentadiene and methyl acrylate

New L-Serine Derivative Ligands as Cocatalysts for Diels-Alder Reaction

Contact Info

Product

Resources

About