The hydroalumination of ω-terbutoxy alkynes an easy access to ω-hydroxy alkenyl iodides application to the synthesis of dienic insect pheromones

Alexakis, Alexandre; Duffault, Jean-Marc

doi:10.1016/s0040-4039(00)82315-1

Cited by 60 publications

(21 citation statements)

References 14 publications

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“…Organoaluminums generated through known hydroalumination of alkynes afforded the amines 7 in good yields (Table ). Reaction of a Z ‐alkenylaluminum reagent 1 d gave the product amine 7 c in low yield, but as a single alkene stereoisomer (d.r.≥19:1). The addition of more equivalents of 1 d or additives, such as THF or trimethylamine, did not improve the yield.…”

Section: Methodsmentioning

confidence: 99%

An Alumino‐Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

Tarasewicz

Ensan

Batey

2018

Chemistry A European J

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Section: Methodsmentioning

confidence: 99%

An Alumino‐Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

Tarasewicz

Ensan

Batey

2018

Chemistry A European J

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“…Although our initial attempts using conventional Stille cross-coupling procedures with the vinyl tin reagent 40 16 were not effective, changing the ligand from triphenylphosphine to triphenylarsine and employing microwave heating readily afforded racemic cis -trikentrin B in 73% yield which was identical in all respects for the physical and spectroscopic data reported for this compound.…”

mentioning

confidence: 87%

Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling

Chandrasoma

Brown

Brassfield

et al. 2013

Tetrahedron Letters

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An efficient total synthesis of the annulated indole natural product (±)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis.

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“…This observation might be due to lower amounts of Al-acetylides present in alanes other than A19 (Figure 3). [26] Hence, Tables 16 and 18 display the results obtained with the two protocols, using L17 and L22, for a variety of nucleoA C H T U N G T R E N N U N G philes and substrates.…”

Section: Optimization Of the Experimental Conditions: We Began Our Inmentioning

confidence: 99%

Formation of Quaternary Stereogenic Centers by Copper‐Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones

Müller

Alexakis

2013

Chemistry A European J

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Alkenylaluminums undergo asymmetric copper-catalyzed conjugate addition (ACA) to β-substituted enones allowing the formation of stereogenic all-carbon quaternary centers. Phosphinamine-copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96% ee) were obtained for the addition of alkenylalanes to β-substituted enones. Two strategies for the generation of the requisite alkenylaluminums were explored allowing for the introduction of aryl- and alkyl-substituted alkenyl nucleophiles. Moreover, alkyl-substituted phosphinamine (SimplePhos) ligands were identified for the first time as highly efficient ligands for the Cu-catalyzed ACA.

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The hydroalumination of ω-terbutoxy alkynes an easy access to ω-hydroxy alkenyl iodides application to the synthesis of dienic insect pheromones

Cited by 60 publications

References 14 publications

An Alumino‐Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

An Alumino‐Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling

Formation of Quaternary Stereogenic Centers by Copper‐Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones

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