2017
DOI: 10.1002/anie.201612574
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Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ‐Carbolines

Abstract: Isocyanides are exceptional building blocks whose wide deployment in multi-component and metal insertion reactions belies their limited availability. Addressing this deficiency is the first conjugate addition-alkylation method. An array of organolithiums, magnesiates, enolates, and metalated nitriles, add conjugately to β- and β, β-disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to… Show more

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Cited by 20 publications
(5 citation statements)
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“…The initial conjugate addition appears to require resonance-stabilizing -substituents. Attempts to perform the cascade with the isocyanosulfone 27, 6 the cyclopropyl-substituted isocyanoalkene 28, 12 and the -sulfanyl isocyanoalkene 29 were unsuccessful (Scheme 4D).…”
Section: Feature Synthesismentioning
confidence: 99%
See 1 more Smart Citation
“…The initial conjugate addition appears to require resonance-stabilizing -substituents. Attempts to perform the cascade with the isocyanosulfone 27, 6 the cyclopropyl-substituted isocyanoalkene 28, 12 and the -sulfanyl isocyanoalkene 29 were unsuccessful (Scheme 4D).…”
Section: Feature Synthesismentioning
confidence: 99%
“…The addition of organolithiums or magnesiates to the isocyanosulfone 4 is representative, illustrating how the reactivity is essentially dictated by the electron-withdrawing group with minimal influence from the isocyanide (Scheme 1b, 4 → 5). 6 The only true conjugate additions to unactivated isocyanoalkenes are the copper(I)-Pyox (8)-catalyzed additions of stabilized, anionic nucleophiles to isocyanoalkenes having -aryl-or -vinyl-substituents (Scheme 1c, 6 → 7). 7…”
mentioning
confidence: 99%
“…More recently, acid catalysed cyclisation of α-indol-2-yl methyl TosMIC derivatives to synthesize heterocycles 19 has been thoroughly studied, including synthesis of carboline alkaloid Ingenine B. 20 Iodine catalysed [3+3] cycloaddition of indolyl alcohol to enaminones 21 and thiourea catalysed iso-Pictet-Spengler reaction of isotryptamine with aldehydes, 22 are some noteworthy contributions in the field.…”
Section: Figure 1 Selected Examples Of Compounds Containing γ-Carboline Corementioning
confidence: 99%
“…However, the use of toxic and expensive metal catalysts has limited their development as environmentfriendly synthetic protocols. More recently, an acid-catalyzed cyclization of α-indol-2-ylmethyl TosMIC (tosylmethyl isocyanide) derivatives to synthesize heterocycles [19] has been thoroughly studied (Scheme 1), including the synthesis of the carboline alkaloid ingenine B [20]. The iodine-catalyzed [3 + 3] cycloaddition of indolyl alcohol to enaminones [21] and the thiourea-catalyzed iso-Pictet-Spengler reaction of isotryptamine with aldehydes [22], are some noteworthy contributions to the field.…”
Section: Introductionmentioning
confidence: 99%