Topic
Annulation
About: Annulation is a research topic. Over the lifetime, 10152 publications have been published within this topic receiving 189701 citations.
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93 citations
TL;DR: The present work represents the first example of a gold-catalyzed annulation with the proximal C=C bond of an N-allenamide, and is distinctly different from the previously observed annulations at the distal C= C bond.
Abstract: A highly enantioselective gold(I)-catalyzed intermolecular annulation of 2-(1-alkynyl)-2-alken-1-ones with N-allenamides is presented. The present work represents the first example of a gold-catalyzed annulation with the proximal C=C bond of an N-allenamide, and is distinctly different from the previously observed annulations at the distal C=C bond. Interestingly, both enantiomers of the products could be obtained in good yields with high regio-, diastereo-, and enantioselectivity by using either diastereomer of a binol-derived phosphoramidite as a chiral ligand.
93 citations
TL;DR: The Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion is reported.
Abstract: We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C—H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C—H bonds was also achieved with remarkable tolerance to the C═C and C≡C bonds.
93 citations
TL;DR: An unprecedented N-heterocyclic carbene-catalyzed annulation of isatin-derived enals and o-hydroxyphenyl-substituted p-quinone methides as bifunctional reagents has been discovered.
93 citations
TL;DR: The palladium-catalyzed annulation of cyclic and bicyclic alkenes, unsaturated cyclopropanes and cyclobutanes, as well as internal alkynes, by functionally substituted aryl or vinylic halides and triflates provides a very versatile route to a wide variety of heterocycles and carbocycles.
Abstract: The palladium-catalyzed annulation of cyclic and bicyclic alkenes; unsaturated cyclopropanes and cyclobutanes; 1,2-, 1,3- and 1,4-dienes; as well as internal alkynes, by functionally substituted aryl or vinylic halides and triflates provides a very versatile route to a wide variety of heterocycles and carbocycles.
93 citations