Topic
Methyl vinyl ketone
About: Methyl vinyl ketone is a research topic. Over the lifetime, 1510 publications have been published within this topic receiving 26839 citations. The topic is also known as: 3-buten-2-one & gamma-oxo-alpha-butylene.
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TL;DR: In this article, oxo esters with pyrrolidine and tetrahydrofuran rings were converted into optically active isobenzofuran and isoindole derivatives.
Abstract: Oxo esters with pyrrolidine and tetrahydrofuran rings were converted into optically active isobenzofuran and isoindole derivatives. The key step of the sequence was a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone and en-amines prepared from the oxo esters and L-valine diethylamide. The chiral auxiliary was cleaved from the products during workup and 1,5-diketones with a quaternary stereocenter are obtained with 97-99% ee. Subsequent annulation reactions were achieved in two steps via the intermediate aldol products.
6 citations
6 citations
TL;DR: Base-catalyzed cyclizations of glutaraldehyde with nitroethane, β-nitropropionic acid, β -nitro-α-methoxypropionic Acid, and methyl vinyl ketone were investigated and the structures of these resulting nitrocycloalkanols were determined.
Abstract: Base-catalyzed cyclizations of glutaraldehyde with nitroethane, β-nitropropionic acid, β-nitro-α-methoxypropionic acid, and methyl vinyl ketone were investigated. The structures of these resulting nitrocycloalkanols were determined by NMR analysis and chemical reactions.
6 citations
6 citations
TL;DR: In this paper, various approaches to synthesize the tropoloisoquinoline alkaloids grandirubrine (1) and imerubrine(2) were investigated, and the results showed that proceeding from the known 8-bromo-5,6,7-trimethoxyisoquinoline (27) proved most efficient.
Abstract: In connection with efforts to develop total syntheses of the tropoloisoquinoline alkaloids grandirubrine (1) and imerubrine (2), preparations of tricyclic ketone (8) and the related ethoxycarbonyl system (47) are described. Of the various approaches to (8) which were investigated, that proceeding from the known 8-bromo-5,6,7-trimethoxyisoquinoline (27) proved most efficient. Thus, conversion of (27), over three steps, into the Reissert anion (37), followed by alkylation of the latter with methyl iodide or ethyl bromoacetate, afforded (38) and (46), respectively. Treatment of compound (38) with sodium ethoxide resulted in regeneration of the isoquinoline nucleus and provided the C1-substituted compound (40). Upon reaction with lithium diisopropylamide, isoquinoline (40) underwent Dieckmann-type cyclization to give compound (8). A similar reaction sequence involving diester (46) afforded enamine (47), the X-ray crystal structure of which is reported. Efforts to effect Robinson annulation of (8) or (47) with methyl vinyl ketone (or a synthetic equivalent), and thereby produce the tetracyclic compound (10), have been unsuccessful.
6 citations