Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans
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DOI: 10.1002/ejoc.201601305
Abstract: Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction conditions. The generality of the… read more here.
Keywords: annulation; acceptor cyclopropanes; lewis acid; donor acceptor ... See more keywords
Donor-Acceptor Cyclopropanes in the Synthesis of Carbocycles.
Sign Up to like & getrecommendations! Published in 2019 at "Chemical record"
DOI: 10.1002/tcr.201800166
Abstract: Donor-acceptor cyclopropanes not only participate in a broad range of ring openings with nucleophiles, electrophiles, radical and red-ox agents, but also are excellent substrates for various (3+n)-cycloaddition and (3+n)-annulation processes. Moreover, under treatment with Lewis… read more here.
Keywords: carbocycles donor; cyclopropanes synthesis; acceptor cyclopropanes; donor acceptor ... See more keywords
IMIDAZOLONE-ACTIVATED DONOR-ACCEPTOR CYCLOPROPANES WITH A PERIPHERAL STEREOCENTER. A STUDY ON STEREOSELECTIVITY OF CYCLOADDITION WITH ALDEHYDES
Sign Up to like & getrecommendations! Published in 2020 at "Chemistry of Heterocyclic Compounds"
DOI: 10.1007/5879
Abstract: Nucleophilic cyclopropanation of arylideneimidazolones possessing a peripheral chiral center and the subsequent fractional crystallization of diastereomers allows access to the compounds with an enantiomerically uniform configuration of the spirocyclic donoracceptor cyclopropane fragment. They were used… read more here.
Keywords: imidazolone activated; cycloaddition; acceptor cyclopropanes; activated donor ... See more keywords
Application of oxygen/nitrogen substituted donor-acceptor cyclopropanes in the total synthesis of natural products
Sign Up to like & getrecommendations! Published in 2017 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2017.01.033
Abstract: Abstract Donor-acceptor (D-A) cyclopropanes show interesting reactivity and high selectivity in the cleavage of one of the cyclopropane bonds. This particular reactivity has been extensively explored in various transformations like cycloaddition, rearrangement and cascade reactions.… read more here.
Keywords: oxygen nitrogen; acceptor cyclopropanes; nitrogen substituted; donor acceptor ... See more keywords
Insertion of S2 into Donor-Acceptor Cyclopropanes: Access to Dithiolanes and Their Conversion to Thietane Dioxides.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00967
Abstract: A facile and efficient route to dithiolanes starting from donor-acceptor cyclopropanes is reported. Potassium p-toluenethiosulfonate has been established as the reagent of choice for this formal insertion of the disulfide moiety. Using this methodology, dithiolanes… read more here.
Keywords: donor acceptor; thietane dioxides; acceptor cyclopropanes; insertion donor ... See more keywords
Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor-Acceptor Cyclopropanes.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c07088
Abstract: The importance of intramolecular constraints in cyclic transition-state geometries is especially pronounced in n-endo-tet cyclizations, where the usual backside approach of a nucleophile to the breaking bond is impossible for the rings containing less than… read more here.
Keywords: endo tet; tet cyclizations; acceptor cyclopropanes; donor acceptor ... See more keywords
Expedient Ni(OTf)2/visible light photoredox-catalyzed annulation of donor-acceptor cyclopropanes with cyclic secondary amines.
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DOI: 10.1039/d2cc02941c
Abstract: The annulative coupling of donor-acceptor cyclopropanes with cyclic secondary amines is reported using the combination of Ni(OTf)2 and visible light assisted eosin Y catalysis for tandem C-N and C-C bond formation. The reaction sequence provides… read more here.
Keywords: acceptor cyclopropanes; secondary amines; donor acceptor; cyclopropanes cyclic ... See more keywords
Asymmetric ring-opening reactions of donor–acceptor cyclopropanes with 1,3-cyclodiones
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DOI: 10.1039/d2ra08257h
Abstract: Asymmetric ring-opening reactions of donor–acceptor cyclopropanes with 1,3-cyclodiones have been established for the synthesis of enantioenriched γ-hydroxybutyric acid derivatives in the presence of Cu(ii)/trisoxazoline catalyst. These reactions offered the desired products in 70% to 93%… read more here.
Keywords: acceptor cyclopropanes; opening reactions; donor acceptor; ring opening ... See more keywords
Synthesis of 1,5-Substituted Pyrrolidin-2-ones from Donor–Acceptor Cyclopropanes and Anilines/Benzylamines
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DOI: 10.3390/molecules27238468
Abstract: We developed a straightforward synthetic route to pharmacologically important 1,5-substituted pyrrolidin-2-ones from donor–acceptor cyclopropanes bearing an ester group as one of the acceptor substituents. This method includes a Lewis acid-catalyzed opening of the donor–acceptor cyclopropane… read more here.
Keywords: acceptor cyclopropanes; acceptor; chemistry; anilines benzylamines ... See more keywords