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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TL;DR: A novel phosphine-catalyzed sequential [2 + 3] and [3 + 2] annulation domino reaction of γ-benzyl-substituted allenoates has been developed and can proceed smoothly to produce the corresponding aza-bicyclo[3,3,0]octane derivatives in good yields and excellent diastereoselectivity.
Abstract: A novel phosphine-catalyzed sequential [2 + 3] and [3 + 2] annulation domino reaction of γ-benzyl-substituted allenoates has been developed. The reaction can proceed smoothly to produce the corresponding aza-bicyclo[3,3,0]octane derivatives in good yields and excellent diastereoselectivity (only one isomer).
65 citations
TL;DR: A concise, enantioselective synthesis of the potent dual orexin inhibitor suvorexant is reported, featuring a mild copper-catalyzed amination, a highly chemoselectives conjugate addition, and a tandem enantiOSElective transamination/seven-membered ring annulation.
65 citations
TL;DR: A Rh(III)-catalyzed intramolecular redox-neutral atom-economic annulation of a tethered alkyne has been developed to efficiently construct 2-amidealkyl indoles with completely reversed regioselectivity by a C-H activation pathway.
Abstract: A Rh(III)-catalyzed intramolecular redox-neutral atom-economic annulation of a tethered alkyne has been developed to efficiently construct 2-amidealkyl indoles with completely reversed regioselectivity by a C-H activation pathway. Furthermore, using the Rh(III)-catalyzed C-H activation/annulation as a key step, a one-pot synthesis of pyrido[1,2-a]indoles has also been developed and applied to a highly efficient formal total synthesis of (±)-goniomitine.
65 citations
TL;DR: A novel atom-efficient catalytic reaction was proposed in this article, which converts imidazolium salts, with N-butenyl, N-substituted butenyl and N-pentenyl substituents, into five-and six-membered fused-ring imidrazolium a...
65 citations
TL;DR: A novel radical-mediated annulation provides polycyclic products with high enantio- and diastereoselectivity in the specific case of methyl-vinyl ketone as well as a stepwise allylation-aryl/alkyl migration.
Abstract: A three-component coupling using lithiated indoles, boronate esters and allylic acetates generates chiral indolines with adjacent quaternary stereocenters. Successful stereocontrol required the use of phosphoramidite ligands not previously described for organopalladium chemistry. Mechanistic studies indicate a monodentate PdL intermediate, and a stepwise allylation-aryl/alkyl migration. A protodeborylation strategy was used to install a C–H bond in place of the C–B bond. A photoredox coupling was used to replace C–B bond with a C–C bond in a highly diastereoselective manner. In the specific case of methyl-vinyl ketone, a novel radical-mediated annulation provides polycyclic products with high enantio- and diastereoselectivity.
65 citations