Hydrogen Bonding-directed Sequential 1,6/1,4-Addition of Heteroatom Nucleophiles onto Electron-deficient 1,3-Diynes

Perera, Erandi Liyanage; Lee, Daesung

doi:10.1039/d2qo01730j

Org. Chem. Front.

2023

DOI: 10.1039/d2qo01730j

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Hydrogen Bonding-directed Sequential 1,6/1,4-Addition of Heteroatom Nucleophiles onto Electron-deficient 1,3-Diynes

Erandi Liyanage Perera

Daesung Lee

Abstract: The hydrogen bonding-directed sequential 1,6/1,4-additions developed herein allow for creating unique heterocycles with structural diversity under mild conditions without using metal catalysts or organometallic reagents.

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2024

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Cited by 1 publication

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Cyclization Reactions of In Situ-Generated Acyl Ketene with Ynones to Form Oxacycles

Liyanage Perera,

Wink,

Luo

et al. 2024

J. Org. Chem.

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Acyl ketenes react with polar unsaturated functional groups to give unique heterocyclic rings, yet reactions with unpolarized unsaturated functional groups have not been reported. Herein, we describe two effective ring-forming reactions between acetyl ketene and electron-deficient alkynes. The first reaction involves in situ tethering between acetyl ketene and nucleophilecontaining 1,3-diynones, which promotes sequential intramolecular 1,6/1,4-additions to generate 2-methylene-2H-pyrans in various yields (24−91%). The other involves a zwitterionic intermediate generated from acetyl ketene and DABCO, which undergoes a Michael addition with terminal alkynyl ketones to generate 3-acyl-4-pyrones (11−79%).

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Cyclization Reactions of In Situ-Generated Acyl Ketene with Ynones to Form Oxacycles

Liyanage Perera,

Wink,

Luo

et al. 2024

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

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Hydrogen Bonding-directed Sequential 1,6/1,4-Addition of Heteroatom Nucleophiles onto Electron-deficient 1,3-Diynes

Abstract: The hydrogen bonding-directed sequential 1,6/1,4-additions developed herein allow for creating unique heterocycles with structural diversity under mild conditions without using metal catalysts or organometallic reagents.

Cited by 1 publication

References 77 publications

Cyclization Reactions of In Situ-Generated Acyl Ketene with Ynones to Form Oxacycles

Cyclization Reactions of In Situ-Generated Acyl Ketene with Ynones to Form Oxacycles

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