Catalytic enantioselective [3+2] and [4+2]-annulation of cyclic <i>N</i>-sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones

Yang, Ji Seon; Kim, Sung-Gon

doi:10.1039/d4cc02734e

Chem. Commun.

2024

DOI: 10.1039/d4cc02734e

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Catalytic enantioselective [3+2] and [4+2]-annulation of cyclic N-sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones

Ji Seon Yang,

Sung-Gon Kim

Abstract: A highly efficient asymmetric [3+2] and [4+2]-annulation of cyclic N-sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones has been developed.

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Cited by 2 publications

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Organocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam N,O-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic N-Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones

Du,

Han,

Wang

et al. 2024

J. Org. Chem.

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A highly stereoselective protocol for the (3 + 2)-annulation of biphenyl-bridged seven-membered cyclic Nsulfonylimines with γ-hydroxy-α,β-unsaturated ketones was developed. The reactions afforded a wide range of chiral [5.7]-fused εsultams bearing N-adjacent 1,3-stereocenters in excellent yields (93−98% yields) and high enantio/diastereoselectivities (up to >99% ee, >20:1 d.r.) and two other examples with alkoxyl groups were obtained in 52−61% yields, 95% ee, and >20:1 d.r. by utilizing organocatalysis with quinine-derived squaramides.

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Organocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam N,O-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic N-Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones

Du,

Han,

Wang

et al. 2024

J. Org. Chem.

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2-((3R,9bS)-5,5-Dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one

Kim,

Kim

2024

Molbank

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A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-cycloaddition of benzo[d]isothiazole 1,1-dioxide with (E)-4-hydroxy-1-phenylbut-2-en-1-one, using a bifunctional squaramide-based chiral catalyst. The reaction yielded 99% of the product with high enantioselectivity and diastereoselectivity (89:11 er and >20:1 dr). The structure of the newly synthesized compound was confirmed by 1H-, 13C-NMR, IR and mass spectral data.

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Catalytic enantioselective [3+2] and [4+2]-annulation of cyclic N-sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones

Abstract: A highly efficient asymmetric [3+2] and [4+2]-annulation of cyclic N-sulfonyl ketimines with γ- or δ-hydroxy-α,β-unsaturated ketones has been developed.

Cited by 2 publications

References 29 publications

Organocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam N,O-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic N-Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones

Organocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam N,O-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic N-Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones

2-((3R,9bS)-5,5-Dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one

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