Reversal of Stereoselectivity in Cycloadditions of Five‐Membered Cyclic Nitrones Derived from Hexoses
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DOI: 10.1002/ejoc.201601488
Abstract: Two five-membered cyclic nitrones derived from hexoses, a newly synthesized D-allo-configured nitrone and an already known D-talo-configured nitrone, have been examined in 1,3-dipolar cycloaddition reactions with vinyl acetate, allyl benzoate, methyl acrylate, acrylonitrile, and vinylene… read more here.
Keywords: cyclic nitrones; membered cyclic; derived hexoses; five membered ... See more keywords
The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines
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DOI: 10.1016/j.tet.2018.07.040
Abstract: Abstract The addition of Lewis acids changes the path of the reaction of N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same… read more here.
Keywords: cyclic azomethine; cyclic nitrones; nitrones cyclic; vinylpyrroles cyclic ... See more keywords
Aziridination of Cyclic Nitrones Targeting Constrained Iminosugars.
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DOI: 10.1021/acs.orglett.7b02283
Abstract: Rare C-7-substituted aziridinyl iminosugars can be synthesized through a short reaction sequence involving 1,3-cycloaddition of cyclic nitrones with alkynes and a Baldwin rearrangement of isoxazolines into bicyclic 2-acylaziridines. The method is efficient and completely diastereoselective,… read more here.
Keywords: constrained iminosugars; nitrones targeting; cyclic nitrones; targeting constrained ... See more keywords
Synthesis of five-membered cyclic nitrones based on the Lewis acid-catalysed [3+2]-annulation reaction of donor-acceptor cyclopropanes with 1,4,2-dioxazoles.
Sign Up to like & getrecommendations! Published in 2018 at "Chemical communications"
DOI: 10.1039/c8cc04656e
Abstract: A novel synthesis of five-membered cyclic nitrones has been developed based on the Lewis acid-catalysed [3+2]-annulation reaction of D-A cyclopropanes with 1,4,2-dioxazoles. Broad substrate scope and generally good yield make this reaction useful in the… read more here.
Keywords: cyclic nitrones; membered cyclic; synthesis five; reaction ... See more keywords