Cycloisomerization is any isomerization in which the cyclic isomer of the substrate is produced in the reaction coordinate. The greatest advantage of cycloisomerization reactions is its atom economical nature, by design nothing is wasted, as every atom in the starting material is present in the product. In most cases these reactions are mediated by a transition metal catalyst, in few cases organocatalysts and rarely do they occur under thermal conditions. These cyclizations are able to be performed with excellent levels of selectivity in numerous cases and have transformed cycloisomerization into a powerful tool for unique and complex molecular construction.[1] Cycloisomerization is a very broad topic in organic synthesis and many reactions that would be categorized as such exist. Two basic classes of these reactions are intramolecular Michael addition and Intramolecular Diels–Alder reactions. Under the umbrella of cycloisomerization, enyne and related olefin cycloisomerizations are the most widely used and studied reactions.[2]
^For a review on cycloisomerization reactions see:
Enantioselective, transition metal catalyzed cycloisomerizations Angela Marinetti, Hélène Jullien and Arnaud Voituriez Chem. Soc. Rev., 2012,41, 4884-4908 doi:10.1039/C2CS35020C, Critical Review .
^Watson, I. D. G.; Toste, F. D. Chem. Sci. 2012, 3, 2899–2919.
and 14 Related for: Cycloisomerization information
and have transformed cycloisomerization into a powerful tool for unique and complex molecular construction. Cycloisomerization is a very broad topic...
points in organic synthesis is seen in the photochemical A/D-corrin cycloisomerization ring closure reaction, which was the key step in the Eschenmoser /...
consecutive three-component oxazole synthesis by an amidation–coupling–cycloisomerization (ACCI) sequence Eugen Merkul and Thomas J. J. Müller Chem. Commun...
reaction[clarification needed] of nitro vinyl furans with various dienophiles: Cycloisomerization of alkyne ortho-substituted phenols: Substituted benzofurans Dibenzofuran...
Volume 45, Issue 22 , Pages 3635 - 3638 2006 Abstract Path b to 3: cycloisomerization with Pd(PPh3)2(OAc)2. Path c to 4: enyne metathesis with Hoveyda–Grubbs...
Structural Reassignment of Anhydrocannabimovone through Gold(I)-Catalyzed Cycloisomerization". Angewandte Chemie. 55 (25) (International Ed. in English ed.): 7121–5...
A/D-corrin-ring closure by photochemical A/D-seco-corrin→corrin cycloisomerization, key step in the ETH Zurich A/D variant of the total synthesis of vitamin...
second model synthesis, published 1969, explored a novel photochemical cycloisomerization process to create the direct A/D-ring junction as final corrin-ring...
Max; Simonneau, Antoine (2011-03-09). "Transition Metal Catalyzed Cycloisomerizations of 1, n -Allenynes and -Allenenes". Chemical Reviews. 111 (3): 1954–1993...
assembly of biphenylyl-naphthalenes and their platinum-catalyzed double cycloisomerization leading to various [6]helicenes: [4]Helicene [5]Helicene [6]Helicene...
Complexes as New Highly Efficient and Air-Stable Catalysts for the Cycloisomerization of Enynes". Organic Letters. 7 (19): 4133–4136. doi:10.1021/ol0515917...
Rodriguez, A. D.; Shi, J.-G. (1998). "The First Cembrane-Pseudopterane Cycloisomerization". J. Org. Chem. 63 (2): 420–421. doi:10.1021/jo971884g. Roethle, P...
Rodriguez, A. D.; Shi, J.-G. (1998). "The First Cembrane-Pseudopterane Cycloisomerization". Journal of Organic Chemistry. 63 (2): 420–421. doi:10.1021/jo971884g...
Enyne cyclization, in particular cycloisomerization, one early example being a 5-exo-dig 1,6 enyne cycloisomerization: cycloaddition reactions with early...
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