Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols

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Abstract: The development of methods to allow the selective acylative dynamic kinetic resolution (DKR) of tetra‐substituted lactols is a recognised synthetic challenge. In this manuscript, a highly enantioselective isothiourea‐catalysed acylative DKR of tetra‐substituted morpholinone and benzoxazinone‐derived lactols is reported. The scope and limitations of this methodology have been developed, with high enantioselectivity and good to excellent yields (up to 89 %, 99: 1 er) observed across a broad range of substrate derivatives incorporating substitution at N (4) and C (2), di‐ and spirocyclic substitution at C (5) and C (6), as well as benzannulation (>35 examples in total). The DKR process is amenable to scale‐up on a 1 g laboratory scale. The factors leading to high selectivity in this DKR process have been probed through computation, with an N−C=O⋅⋅⋅isothiouronium interaction identified as key to producing ester products in highly enantioenriched form.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols ; day:06 ; month:08 ; year:2024 ; extent:11
Angewandte Chemie / International edition. International edition ; (06.08.2024) (gesamt 11)

Creator: Zhu, Haoxiang
Manchado, Alejandro
Omar Farah, Abdikani
McKay, Aidan P.
Cordes, David B.
Cheong, Paul Ha‐Yeon
Kasten, Kevin
Smith, Andrew D.

DOI: 10.1002/anie.202402908

URN: urn:nbn:de:101:1-2408061435549.201347263642

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:02 AM CEST

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Zhu, Haoxiang
Manchado, Alejandro
Omar Farah, Abdikani
McKay, Aidan P.
Cordes, David B.
Cheong, Paul Ha‐Yeon
Kasten, Kevin
Smith, Andrew D.

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Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Hochschulschrift

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Hochschulschrift

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Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Aufsatzsammlung

Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)

Accessing Indenoazulenes via a Gold‐Catalysed Cyclisation of Cycloheptatrienyl‐Substituted 1,5‐Diynes

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Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols

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Other Objects (12)

Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols

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Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)

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Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

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Synthesis of Substituted 1-Deazapurines via Pd/Cu Catalysed C-H Activation, Substituted Naphthyridines, Quinoxalines, and Trifluoromethyl-Substituted Arenes by Pd(0)-Catalysed Cross-Coupling Reactions

Isothiourea‐Catalysed Acylative Kinetic Resolution of Tertiary Pyrazolone Alcohols

Isothiourea‐Catalysed Acylative Kinetic Resolution of Tertiary Pyrazolone Alcohols

Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)

Accessing Indenoazulenes via a Gold‐Catalysed Cyclisation of Cycloheptatrienyl‐Substituted 1,5‐Diynes

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Synthesis of Tetra‐Substituted 3‐Hydroxyphthalide Esters by Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution

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Isothiourea‐Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp 2 vs. sp 2) Substituted Secondary Alcohols

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Synthesis of substituted 1-deazapurines via Pd/Cu catalysed C-H activation, substituted naphthyridines, quinoxaklines, trifluoromethyl-substituted arenes by Pd(0)-catalysed cross-coupling reactions

Synthesis of Substituted 1-Deazapurines via Pd/Cu Catalysed C-H Activation, Substituted Naphthyridines, Quinoxalines, and Trifluoromethyl-Substituted Arenes by Pd(0)-Catalysed Cross-Coupling Reactions

Isothiourea‐Catalysed Acylative Kinetic Resolution of Tertiary Pyrazolone Alcohols

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Selective Ring‐Opening of Di‐Substituted Epoxides Catalysed by Halohydrin Dehalogenases

Dynamic Kinetic Resolution (DKR) and Dynamic Kinetic Asymmetric Transformations (DYKAT)

Accessing Indenoazulenes via a Gold‐Catalysed Cyclisation of Cycloheptatrienyl‐Substituted 1,5‐Diynes

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