Base‐Promoted [3+3]‐Cycloaddition of γ‐Hydroxy‐α,β‐unsaturated Carbonyls with <i>N,N′</i>‐Cyclic Azomethine Imines for Synthesizing Bicyclic Oxadiazines

Kang, Sung Hyun; Park, Byung Jun; Kim, Sung‐Gon

doi:10.1002/ejoc.202200867

Eur J Org Chem

2022

DOI: 10.1002/ejoc.202200867

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Base‐Promoted [3+3]‐Cycloaddition of γ‐Hydroxy‐α,β‐unsaturated Carbonyls with N,N′‐Cyclic Azomethine Imines for Synthesizing Bicyclic Oxadiazines

Sung Hyun Kang

Byung Jun Park

Sung‐Gon Kim

Abstract: A novel approach of [3+3]‐cycloaddition of N,N′‐cyclic azomethine imines with γ‐hydroxy‐α,β‐unsaturated carbonyls was developed. Bicyclic oxadiazines were readily obtained in moderate to good yields from the reactions of various γ‐hydroxy‐α,β‐unsaturated ketones, including aromatic and aliphatic ketones, with N,N′‐cyclic azomethine imines under mild conditions, demonstrating the broad substrate scope.

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2023

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Cited by 4 publications

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Organocatalytic Enantioselective Synthesis of 1,3‐Oxazinanes and Hexahydropyrimidines via [4+2]‐Annulation of CyclicN‐Sulfimines

Kim

2023

Asian J Org Chem

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The first asymmetric synthetic method for enantioenriched 1,3‐oxazinane and hexahydropyrimidine derivatives via the asymmetric [4+2]‐annulation of cyclic N‐sulfimines has been established. The reaction of cyclic N‐sulfimines with δ‐hydroxy‐α,β‐unsaturated ketones afforded a wide range of enantioenriched polyheterotricyclic 1,3‐oxazinane derivatives in high yields with good to excellent enantioselectivities in the presence of a cinchonidine‐derived squaramide catalyst. This approach has been extended to the asymmetric organocatalytic [4+2]‐annulation of cyclic N‐sulfimines with δ‐NHTs‐α,β‐unsaturated ketones providing enantioenriched hexahydropyrimidines. In addition, the asymmetric [4+2]‐annulation of δ‐hydroxy‐ and δ‐NHTs‐α,β‐unsaturated ketones gave their corresponding enantioenriched 1,3‐oxazinane and hexahydropyrimidine derivatives with different absolute configurations.

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Organocatalytic Enantioselective Synthesis of 1,3‐Oxazinanes and Hexahydropyrimidines via [4+2]‐Annulation of CyclicN‐Sulfimines

Kim

2023

Asian J Org Chem

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Base‐catalyzed [3 + 2]/[4 + 2]‐annulations of cyclic N‐sulfimines with γ‐ and δ‐sulfonamido/hydroxy‐α,β‐unsaturated carbonyls: Stereoselective synthesis of imidazolidines, oxazolidines, hexahydropyrimidines, and 1,3‐oxazinanes

Kim

2023

Bulletin Korean Chem Soc

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A highly efficient and straightforward synthetic methodology has been established for the preparation of imidazolidine derivatives through the [3 + 2]‐annulation of cyclic N‐sulfimines. This reaction involves the reaction of cyclic N‐sulfimines and γ‐sulfonamido‐α,β‐unsaturated carbonyl compounds, with Cs2CO3 serving as the catalyst. The outcome is a diverse range of imidazolidine derivatives with remarkable yields and stereoselectivities. In addition, the [4 + 2]‐annulation between cyclic N‐sulfimines and δ‐sulfonamido‐α,β‐unsaturated carbonyl compounds, catalyzed by Et3N, has been successfully applied for the synthesis of stereoselective hexahydropyrimidines. Furthermore, the base‐catalyzed annulation of cyclic N‐sulfimines with γ‐ and δ‐hydroxy‐α,β‐unsaturated carbonyl compounds has proven to be a reliable method for the synthesis of oxazolines and 1,3‐oxazinanes.

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Enantioselective Synthesis of Diazobicyclic Oxadiazines via Organocatalytic [3+3]-Cycloaddition of γ-Hydroxy-α,β-Unsaturated Carbonyls with N,N′-Cyclic Azomethine Imines

Kim¹,

Kang²,

Park³

2023

Synthesis

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A diastereo- and enantioselective synthesis of diazobicyclic oxadiazines was developed through an organocatalytic cycloaddition reaction. Asymmetric catalytic [3+3]-cycloaddition of γ-hydroxy-α,β-unsaturated carbonyls with N,N′-cyclic azomethine imines, using a squaramide-based catalyst, provided biologically important enantioenriched diazobicyclic oxadiazines in good yields with moderate to high diastereo- and enantioselectivities (up to 10:1 dr and 79:21 er).

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Base‐Promoted [3+3]‐Cycloaddition of γ‐Hydroxy‐α,β‐unsaturated Carbonyls with N,N′‐Cyclic Azomethine Imines for Synthesizing Bicyclic Oxadiazines

Cited by 4 publications

References 43 publications

Organocatalytic Enantioselective Synthesis of 1,3‐Oxazinanes and Hexahydropyrimidines via [4+2]‐Annulation of CyclicN‐Sulfimines

Organocatalytic Enantioselective Synthesis of 1,3‐Oxazinanes and Hexahydropyrimidines via [4+2]‐Annulation of CyclicN‐Sulfimines

Base‐catalyzed [3 + 2]/[4 + 2]‐annulations of cyclic N‐sulfimines with γ‐ and δ‐sulfonamido/hydroxy‐α,β‐unsaturated carbonyls: Stereoselective synthesis of imidazolidines, oxazolidines, hexahydropyrimidines, and 1,3‐oxazinanes

Enantioselective Synthesis of Diazobicyclic Oxadiazines via Organocatalytic [3+3]-Cycloaddition of γ-Hydroxy-α,β-Unsaturated Carbonyls with N,N′-Cyclic Azomethine Imines

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