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: The copper(I)-catalyzed regioselective [3 + 2] cyclization of pyridines toward alkenyldiazoacetates leading to functionalized indolizine derivatives is reported.
Abstract: The copper(I)-catalyzed regioselective [3 + 2] cyclization of pyridines toward alkenyldiazoacetates leading to functionalized indolizine derivatives is reported. A broad range of pyridine derivatives (including quinoline and isoquinoline) is compatible with this cyclization reaction. The process represents the first successful example of metal-catalyzed cyclization of a π-deficient heterocyclic system with alkenyldiazo compounds.
168 citations
TL;DR: Highly enantioselective annulation of activated alkenes with α-substituted allenoates catalyzed by amino acid-based bifunctional phosphines has been developed for the first time, which provides an easy access to optically enriched functionalized cyclohexenes.
Abstract: Highly enantioselective [4 + 2] annulation of activated alkenes with α-substituted allenoates catalyzed by amino acid-based bifunctional phosphines has been developed for the first time, which provides an easy access to optically enriched functionalized cyclohexenes. In particular, 3-spirocyclohexene-2-oxindoles were prepared in high yields and with excellent enantioselectivities.
166 citations
TL;DR: The synthesis and cellular profiling of chiral organosilicon small molecules derived from a crotylsilane annulation pathway are described and it is considered that incorporating a main-group element within the chiral environment of a more complex product could provide new structures.
Abstract: Small-molecule synthesis coupled with cellular profiling using multidimensional screening can be used to assess the impact of varying stereochemical and appendage contexts on biological activity. In this communication, we describe the synthesis and cellular profiling of chiral organosilicon small molecules derived from a crotylsilane annulation pathway. We considered that incorporating a main-group element, such as silicon, within the chiral environment of a more complex product could provide new structures where the distinctive chemical properties of silicon may contribute to new biological activity. The annulation of various indole-2,3-dione (isatin) reagents with functionalized crotylsilanes provides efficient access to spiro-oxindole structures for biological evaluation. The modular placement of aryl iodide functional groups in the isatin component can be used in appending processes for further substitution, such as conversion of the aryl iodide to various amido functionalities using the Buchwald amid...
166 citations
TL;DR: In this article, a general strategy for the synthesis of highly substituted polycyclic aromatic and heteroaromatic compounds was developed, which is achieved simply by the irradiation of a dichloroethane solution of an acetylene derivative and a vinyl or aryl α-diazo ketone.
Abstract: A general strategy for the synthesis of highly substituted polycyclic aromatic and heteroaromatic compounds has been developed. The new aromatic annulation is achieved simply by the irradiation of a dichloroethane solution of an acetylene derivative and a vinyl or aryl α-diazo ketone. Mechanistically, the reaction proceeds via the photochemical Wolff rearrangement of the diazo ketone to generate an aryl- or vinylketene, followed by a cascade of three pericyclic reactions. A variety of substituted phenols, naphthalenes, benzofurans, benzothiophenes, indoles, and carbazoles can be prepared by using the method
166 citations
165 citations