Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition
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Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition.
Simple haloaldehydes, including enolisable aldehydes, were found to be suitable for the formation of cyclic products by cascade (domino) condensation, cyclisation, dipolar cycloaddition chemistry. This multi-component reaction approach to heterocyclic compounds was explored by using hydroxylamine, a selection of aldehydes, and a selection of activated dipolarophiles. Initial condensation gives ...
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An efficient stereocontrolled route to ( )-cylindricine C is described. Reaction of 9-hydroxynon-1-en-5one oxime with 2,3-bis(phenylsulfonyl)-1,3-butadiene affords a 7-oxa-1-azanorbornane cycloadduct in high yield. The formation of the bicyclic isoxazolidine arises from conjugate addition of the oxime onto the diene to give a transient nitrone that spontaneously undergoes an intramolecular dipo...
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A catalytic method involving carbenoid insertion onto dihydroimidazoles is reported for the generation of dihydroimidazolium ylides, and their subsequent diastereoselective cycloaddition to form pyrrolo[1,2-a]imidazoles © 2009 Elsevier Science. All rights reserved ———
متن کاملCycloaddition of homochiral dihydroimidazoles: a 1,3-dipolar cycloaddition route to optically active pyrrolo[1,2-a]imidazoles.
N-Alkylation of optically active 1-benzyl-4-phenyl-4,5-dihydroimidazole with active alkyl halides and treatment of the so-formed 4,5-dihydroimidazolium ions with DBU in the presence of a range of electron-deficient alkene dipolarophiles, constitutes a 'one-pot' cascade terminating in a 1,3-dipolar cycloaddition reaction that affords optically active pyrrolo[1,2-a]imidazoles. Three bonds of the ...
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ژورنال
عنوان ژورنال: Org. Biomol. Chem.
سال: 2016
ISSN: 1477-0520,1477-0539
DOI: 10.1039/c6ob01871h