[4 + 2] Annulation of δ-Hydroxy/δ-Sulfonamido-α,β-Unsaturated Ketones with Azlactones for Diastereoselective Synthesis of Highly Substituted 3-Amino-δ-Lactones and 3-Amino-δ-Lactams

Kim, Heebum; Kim, Sung‐Gon

doi:10.1021/acs.joc.3c00065

Cited by 6 publications

References 42 publications

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The Pyrrolidine‐Catalyzed Three‐Component Reactions of Azlactones,N,O‐Acetals and Alcohols: One‐Pot Synthesis of α,β‐Diamino Esters

Wang

et al. 2023

Adv Synth Catal

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A pyrrolidine‐catalyzed three‐component reaction of azlactone, N,O‐acetal and alcohol for the synthesis of α,β‐diamino ester was reported. The N,O‐acetal served as the imine equivalent to occur Mannich reaction with azlactone, and the in situ generated α‐functionalized azlactone subsequently underwent a ring‐opening process in the presence of alcohol. A series of α,β‐diamino esters were obtained in 36–99% yields under mild reaction conditions. The product could be synthesized on gram‐scale and transformed into the α,β‐diamino acid.

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The Pyrrolidine‐Catalyzed Three‐Component Reactions of Azlactones,N,O‐Acetals and Alcohols: One‐Pot Synthesis of α,β‐Diamino Esters

Wang

et al. 2023

Adv Synth Catal

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Asymmetric Synthesis of 3,4‐Dihydroquinolin‐2‐ones via Organocatalytic [4+2]‐Cyclization of 2‐Amino‐β‐nitrostyrenes with Azlactones

Kim,

Kim

2024

Adv Synth Catal

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Dihydroquinolin‐2‐ones, recognized for their significant bioactive properties, feature a unique six‐membered structure with nitrogen‐containing heterocycles. A breakthrough method has been developed to synthesize enantioenriched 3,4‐dihydroquinoline‐2‐one derivatives. This innovative approach utilizes an asymmetric [4+2]‐cyclization process, combining 2‐amino‐β‐nitrostyrenes with azlactones, and is facilitated by a bifunctional squaramide‐based organocatalyst. This innovative approach has enabled the creation of novel chiral 3,4‐dihydroquinoline‐2‐ones with complex structures, including chiral quaternary centers. The process is remarkably efficient, delivering high yields (up to 91%), excellent enantiomeric excess (up to 97% ee), and superior diastereoselectivity (up to 19:1 dr).

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Catalytic Asymmetric [4+2] Cyclization of Hydroxyphenyl Indolinone with Azlactone to Construct Spirooxindole δ‐Lactone

Wang,

Ren

2024

Chin. J. Chem.

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Comprehensive SummaryAn efficient asymmetric [4+2] cyclization of hydroxyphenyl indolinone with azlactone for the synthesis of spirooxindole δ‐lactone has been developed, which realized the first asymmetric reaction of hydroxyphenyl indolinone. A series of intricate structures with congested vicinal quaternary chiral centers were provided in good yields with excellent enantioselectivities via the in situ generated o‐QM from hydroxyphenyl indolinone.

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[4 + 2] Annulation of δ-Hydroxy/δ-Sulfonamido-α,β-Unsaturated Ketones with Azlactones for Diastereoselective Synthesis of Highly Substituted 3-Amino-δ-Lactones and 3-Amino-δ-Lactams

Cited by 6 publications

References 42 publications

The Pyrrolidine‐Catalyzed Three‐Component Reactions of Azlactones,N,O‐Acetals and Alcohols: One‐Pot Synthesis of α,β‐Diamino Esters

The Pyrrolidine‐Catalyzed Three‐Component Reactions of Azlactones,N,O‐Acetals and Alcohols: One‐Pot Synthesis of α,β‐Diamino Esters

Asymmetric Synthesis of 3,4‐Dihydroquinolin‐2‐ones via Organocatalytic [4+2]‐Cyclization of 2‐Amino‐β‐nitrostyrenes with Azlactones

Catalytic Asymmetric [4+2] Cyclization of Hydroxyphenyl Indolinone with Azlactone to Construct Spirooxindole δ‐Lactone

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