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• W80861644 endingPage "137" @default.
• W80861644 startingPage "69" @default.
• W80861644 abstract "The 1,4-conjugate addition of stabilized carbanions (1,3-dicarbonyl class) to α,β-unsaturated carbonyl compounds was reported by Michael in 1887 and quickly became established as an efficient method for carboncarbon bond formation.1 Numerous stabilized nucleophiles (donors) have been found to participate efficiently in 1,4-conjugate additions to other activated alkenes (acceptors).2 In general, the reactivity of acceptors (a3-synthons) towards various stabilized carbanions follows: α,β-unsaturated aldehydes >> α,β-unsaturated ketones > α,β-unsaturated nitriles > α,β-unsaturated esters > α,β-unsaturated amides.3 Although the basic synthetic principles and reactivity were investigated in early years, limitations to this versatile form of carboncarbon bond formation were observed. For example, the addition of organolithiums or organomagnesium halides to α,β-unsaturated aldehydes affords exclusive 1,2addition, while additions to α,β-unsaturated ketones afford predominant 1,2-addition. During the last four decades intensive research in the use of unstabilized carbon nucleophiles for 1,4-conjugate additions was stimulated by three events. First, Kharasch and Tawney reported that preferential 1,4-conjugate addition of alkylmagnesium halides to isophorone was effected by catalytic amounts of copper(I) chloride,4 and second, House, Respess and Whitesides showed that the actual reactive species in the earlier work was an organocopper species.5 Third, Gilman and Kirby reported a comparative study of the addition of various aryl metallics to benzalacetophenone (1,3-diphenylpropene-1-one) in which several Group II (R2Cd and R2Zn) and Group III (R3Al) organometallics afforded exclusive 1,4-conjugate addition.6" @default.
• W80861644 created "2016-06-24" @default.
• W80861644 creator A5059048373 @default.
• W80861644 date "1991-01-01" @default.
• W80861644 modified "2023-10-09" @default.
• W80861644 title "Conjugate Additions of Reactive Carbanions to Activated Alkenes and Alkynes" @default.
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