Azetidine synthesis by La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines

Kuriyama, Yuse; Sasano, Yusuke; Iwabuchi, Yoshiharu

doi:10.3389/fchem.2023.1251299

Front. Chem.

2023

DOI: 10.3389/fchem.2023.1251299

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Azetidine synthesis by La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines

Yuse Kuriyama,

Yusuke Sasano,

Yoshiharu Iwabuchi

Abstract: Azetidine is a prevalent structural motif found in various biologically active compounds. In this research paper, we report La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines to afford azetidines. This reaction proceeded in high yields even in the presence of acid-sensitive and Lewis basic functional groups.

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2024

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A General and Scalable Method toward Enantioenriched C2-Substituted Azetidines Using Chiral tert-Butanesulfinamides

Zelch,

Russo,

Ruud

et al. 2024

J. Org. Chem.

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Diverse ranges of chiral nitrogen-containing heterocycles serve as a molecular toolbox for modulating a wide array of biological processes, but enantioenriched production of smaller chiral heterocycles is a bottleneck. There is a lack of general approaches for the stereoselective preparation of chiral 4membered monocyclic C2-substituted azetidines, where many routes to different substitution types are possible, but no simple and common approach exists. To bridge this gap, inexpensive and widely available chiral tert-butanesulfinamides are harnessed for chiral induction with 1,3-bis-electrophilic 3-chloropropanal, providing a three-step approach to C2-substituted azetidines with aryl, vinyl, allyl, branched alkyl, and linear alkyl substituents. Eleven azetidine products are produced, and the approach is shown to be effective on a gram-scale with a single purification of the protected azetidine product in 44% yield over three steps in an 85:15 diastereomeric ratio. In most cases, the diastereomers are separable using normal phase chromatography, often resulting in previously elusive enantiopure azetidine products. Protected azetidines were shown to undergo rapid and efficient sulfinamide cleavage, producing an azetidine hydrochloride salt that was subjected to derivatization reactions, highlighting the method's applicability to medicinal chemistry approaches.

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A General and Scalable Method toward Enantioenriched C2-Substituted Azetidines Using Chiral tert-Butanesulfinamides

Zelch,

Russo,

Ruud

et al. 2024

J. Org. Chem.

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show abstract

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Azetidine synthesis by La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines

Cited by 1 publication

References 30 publications

A General and Scalable Method toward Enantioenriched C2-Substituted Azetidines Using Chiral tert-Butanesulfinamides

A General and Scalable Method toward Enantioenriched C2-Substituted Azetidines Using Chiral tert-Butanesulfinamides

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