Isothiourea‐Catalysed Acylative Dynamic Kinetic Resolution of Tetra‐substituted Morpholinone and Benzoxazinone Lactols
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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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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)
- Urheber
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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.
- DOI
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10.1002/anie.202402908
- URN
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urn:nbn:de:101:1-2408061435549.201347263642
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 11:02 MESZ
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Beteiligte
- 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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