Diels–Alder Reactions of 1,2-Dihydropyridines: An Efficient Tool for the Synthesis of Isoquinuclidines

Synthesis ◽  
2018 ◽  
Vol 50 (09) ◽  
pp. 1773-1782 ◽  
Author(s):  
Eduarda Silva ◽  
Artur Silva ◽  
Djenisa Rocha
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Tool ◽  
Organometallic Catalysts ◽  
Diels Alder Reaction ◽  
Straightforward Method ◽  
Recent Developments ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Valuable Compounds

The Diels–Alder reaction of 1,2-dihydropyridines with different dienophiles is a well-established and straightforward method for the synthesis of isoquinuclidines. Nevertheless, the enantioselective preparation of isoquinuclidines using organocatalysts or organometallic catalysts is rather unexplored. This succinct review offers readers an overall perspective of the most important recent developments and concepts related to this topic.1 Introduction2 Asymmetric Diels–Alder Reaction of 1,2-Dihydropyridines2.1 Transition-Metal-Catalyzed Reactions2.2 Organocatalyzed Reactions3 Diels–Alder Reaction of 1,2-Dihydropyridines in the Synthesis of Biologically Valuable Compounds4 Conclusion

ChemInform Abstract: Recent Developments in the retro-Diels-Alder Reaction

ChemInform ◽  
2013 ◽  
Vol 44 (33) ◽  
pp. no-no
Author(s):  
Sambasivarao Kotha ◽  
Shaibal Banerjee
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Recent Developments

ChemInform Abstract: Ionic Diels-Alder Reaction: Recent Developments

ChemInform ◽  
2010 ◽  
Vol 30 (49) ◽  
pp. no-no
Author(s):  
Rashmi Sanghi ◽  
Padma S. Vankar ◽  
Yashwant D. Vankar
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Recent Developments

scholarly journals Natural amino acids as chiral auxiliaries in asymmetric Diels–Alder reactions

1988 ◽  
Vol 66 (11) ◽  
pp. 2826-2829 ◽  
Author(s):  
Maria P. Bueno ◽  
Carlos Cativiela ◽  
José A. Mayoral ◽  
Alberto Avenoza ◽  
Paula Charro ◽  
...  
Keyword(s):  
Amino Acids ◽  
Structural Similarity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Isopropyl Ester ◽  
Chiral Auxiliaries ◽  
Titanium Catalysts ◽  
Diels Alder Reaction ◽  
Catalyzed Reactions ◽  
Natural Amino Acids

To test whether α-amino acids can be efficient chiral auxiliaries in asymmetric Diels–Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene. Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1R,2R)-cycloadduct were achieved with AlCl3, the reaction did not show diastereofacial selectivity when titanium catalysts were used. Moreover, with Ti(iPrO)4 a transesterification reaction, which leads to the isopropyl ester and competes with the Diels–Alder reaction, was observed. In spite of the structural similarity of this dienophile to the acrylate of (S)-ethyl lactate, it behaved very differently in the titanium-catalyzed reactions.

Organometallic catalysts in synthetic organic chemistry: From reactions in aqueous media to gold catalysis

2008 ◽  
Vol 80 (5) ◽  
pp. 831-844 ◽  
Author(s):  
Jean-Pierre Genêt ◽  
Sylvain Darses ◽  
Véronique Michelet
Keyword(s):  
Aqueous Media ◽  
Gold Catalysis ◽  
Catalytic Reactions ◽  
Organometallic Catalysts ◽  
Water As Solvent ◽  
Recent Developments ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Simplified Procedures ◽  
Significant Attention

Water has attracted significant attention as an alternative solvent for transition-metal-catalyzed reactions. The use of water as solvent allows simplified procedures for separation of the catalyst from the products and recycling of the catalyst. Water is an inexpensive reagent for the formation of oxygen-containing products such as alcohols. The use of water as a medium for promoting organometallic and organic reactions is also of great potential. This chapter will focus on old and recent developments in the design and applications of some catalytic reactions using aqueous-phase Pd, Rh, Pt, and Au complexes.

Facial selective Diels–Alder reactions of (1R,5R)-(+)-3-carbomethoxy-6,6-dimethylbicyclo[3.1.1]hept-3-en2-one. Unusual ketalization–fragmentation reaction of adducts

1994 ◽  
Vol 72 (5) ◽  
pp. 1193-1210 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Sew Yeu Chew ◽  
Eric N. C. Browne ◽  
Jeung Bea Kim
Keyword(s):  
High Selectivity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ambient Temperatures ◽  
Diels Alder Reaction ◽  
Unexpected Reaction ◽  
Catalyzed Reactions ◽  
High Yields ◽  
Cyclobutane Ring ◽  
Steric Influence

The stereofacially differentiated enone ester 5 has been used to study the effects of steric influence on the Diels–Alder reaction. In general, under Lewis acid catalysis, 5 adds to dienes at low to ambient temperatures in a reasonable rate. Yields of predictable chiral adducts are moderate with the unexpected exception of zinc chloride catalyzed reactions, which provide good to high yields. In all cases only products of addition to the Si face of general type 21 were observed. The regiochemistry of the adducts is exclusively that predicted by the ortho and para rules. The stereochemistry shows a high selectivity in favor of ester-endo transition state products. Rationales for the observed stereoselectivities are discussed. The fragmentation of adducts of 5, in particular keto ester 9, has been briefly examined. Olefins 30 and 46 derived from 9 have been converted to ring-opened cadinane skeletons 31 and 47, respectively, by conditions we have previously reported. In an entirely new and unexpected reaction, simultaneous ketalization and fragmentation of the cyclobutane ring of ketones derived from 9 gave ring-opened ketals 34 + 35 (from 29), 36 + 37 (from 9), 39 (from 38) and 42 + 43 (from 40).

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