Rapid Synthesis of Carbohydrate Derivatives, Including Mimetics ofC-Linked Disaccharides andC-Linked Aza Disaccharides, Using the Hetero-Diels−Alder Reaction

2010 ◽  
Vol 75 (21) ◽  
pp. 7210-7218 ◽  
Author(s):  
Peter A. Burland ◽  
David Coisson ◽  
Helen M. I. Osborn
2019 ◽  
Vol 4 (2) ◽  
pp. 362-367 ◽  
Author(s):  
Renan Galaverna ◽  
Lucas P. Fernandes ◽  
Duncan L. Browne ◽  
Julio C. Pastre

A Diels–Alder reaction employing terpenes for rapid synthesis of monomer libraries under flow conditions is presented.


2011 ◽  
Vol 7 ◽  
pp. 1007-1013 ◽  
Author(s):  
Boubacar Sow ◽  
Gabriel Bellavance ◽  
Francis Barabé ◽  
Louis Barriault

The rapid synthesis of bicyclo[m.n.1]alkanone cores possessing quaternary carbon centers adjacent to a bridged ketone represents a significant synthetic challenge. This type of architectural feature is embedded in various complex biologically active compounds such as hyperforin and garsubellin A. Herein, we report a highly diastereoselective one-pot Diels–Alder reaction/Au(I)-catalyzed carbocyclization to generate bicyclo[3.3.1]alkanones in yields ranging from 48–93%.


Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>


2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand

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