Phosphine-Catalyzed Dearomative [3 + 2] Cycloaddition of Benzoxazoles with a Cyclopropenone
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DOI: 10.1021/acs.orglett.1c04045
Abstract: The triphenylphosphine-catalyzed dearomative [3 + 2] cycloaddition of benzoxazoles with 1,2-diphenylcyclopropenone is herein described. The reaction scope, mechanism, and possible future applications of this rare organocatalyzed cycloaddition are herein discussed. read more here.
Keywords: cycloaddition benzoxazoles; catalyzed dearomative; benzoxazoles cyclopropenone; dearomative cycloaddition ... See more keywords
Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
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DOI: 10.1021/acs.orglett.2c02983
Abstract: The dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations furnish cyclohepta[b]indoles, functionality-rich frameworks found in many bioactive compounds, including all pentacyclic ambiguine alkaloids. The analogous reactions between oxyallyl cations and… read more here.
Keywords: reactions alkenylindoles; alkenylpyrroles afford; dearomative cycloaddition; cyclohepta indoles ... See more keywords
Diastereo- and Enantioselective Dearomative [3 + 2] Cycloaddition Reaction of 2-Nitrobenzofurans with 3-Isothiocyanato Oxindoles.
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DOI: 10.1021/acs.orglett.7b03667
Abstract: Enantioselective dearomative [3 + 2] cycloaddition reaction of 2-nitrobenzofurans with 3-isothiocyanato oxindoles was developed. The reaction employs a chiral bis(oxazoline)/Zn(OTf)2 catalyst, allowing a practical, straightforward access to structurally diverse spirooxindoles containing a 2,3-dihydrobenzofuran motif and… read more here.
Keywords: dearomative cycloaddition; reaction nitrobenzofurans; nitrobenzofurans isothiocyanato; reaction ... See more keywords
Silver-promoted dearomative [3+4] cycloaddition of anthranils with α-isocyanoacetates: access to benzodiazepines.
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DOI: 10.1039/d2cc00807f
Abstract: The first example of silver-promoted [3+4] cycloaddition of α-isocyanoacetates with anthranils as aromatic Michael accepters, offering access to benzo[d][1,3]diazepinones, has been developed. Mechanistic studies revealed that an "oxygen migration" rearrangement process was involved in this… read more here.
Keywords: dearomative cycloaddition; cycloaddition anthranils; silver promoted; promoted dearomative ... See more keywords
Intermolecular dearomative [4 + 2] cycloaddition of naphthalenes via visible-light energy-transfer-catalysis
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DOI: 10.1039/d2sc04005k
Abstract: The dearomative cycloaddition reaction serves as a blueprint for creating sp3-rich three-dimensional molecular topology from flat-aromatic compounds. However, severe reactivity and selectivity issues make this process arduous. Herein, we describe visible-light energy-transfer catalysis for the… read more here.
Keywords: energy transfer; dearomative cycloaddition; transfer catalysis;
Regiodivergent catalytic asymmetric dearomative cycloaddition of bicyclic heteroaromatics
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DOI: 10.1126/sciadv.adg1645
Abstract: The catalytic dearomative cycloaddition of bicyclic heteroaromatics including benzofurans and indoles provides rapid access to functionalized heterocyclic molecules. Because of the inherent stereoelectronic differences, the furan or pyrrole nucleus is more prone to dearomative cycloaddition… read more here.
Keywords: cycloaddition bicyclic; cycloaddition; dearomative cycloaddition; bicyclic heteroaromatics ... See more keywords
Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes
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DOI: 10.1126/science.abg0720
Abstract: Heteroaromatics lured into cycloadditions The Diels-Alder reaction is widely used to produce six-membered carbon rings from alkenes and dienes. Heteroaromatics such as quinolines resemble dienes in principle, but in practice their pairs of double bonds… read more here.
Keywords: dearomative cycloaddition; intermolecular dearomative; cycloaddition; bicyclic azaarenes ... See more keywords