Enantioselective Synthesis of Oxazocines via MQ-Phos Enabled Palladium-Catalyzed Asymmetric Formal [4+4]-Cycloadditions.
MQ‐Phos ligand
[4+4]‐cycloaddition
enantioselectivity
medium‐sized ring
palladium catalysis
Journal
Advanced science (Weinheim, Baden-Wurttemberg, Germany)
ISSN: 2198-3844
Titre abrégé: Adv Sci (Weinh)
Pays: Germany
ID NLM: 101664569
Informations de publication
Date de publication:
17 Jun 2024
17 Jun 2024
Historique:
revised:
03
05
2024
received:
29
02
2024
medline:
17
6
2024
pubmed:
17
6
2024
entrez:
17
6
2024
Statut:
aheadofprint
Résumé
Oxazocines are key structural intermediates in the synthesis of natural products and pharmaceutical molecules. However, the synthesis of oxazocines especially in a highly enantioselective manner, is a long-standing formidable challenge due to unfavorable energetics involved in cyclization. Herein, a series of new PNP-Ligand P-chiral stereocenter is first designed and synthesized, called MQ-Phos, and successfully applied it in the Pd-catalyzed enantioselective higher-order formal [4+4]-cycloaddition of α, β-unsaturated imines with 2-(hydroxymethyl)-1-arylallyl carbonates. The reaction features mild conditions, excellent regio- and enantiocontrol and a broad substrate scope (54 examples). Various medium-sized rings can be afforded in moderate to excellent yields (up to 92%) and excellent enantioselectivity (up to 99% ee). The newly developed MQ-Phos is critical for synthesis of the medium-sized ring in excellent catalytic reactivity and enantioselectivity.
Identifiants
pubmed: 38885373
doi: 10.1002/advs.202402170
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2402170Subventions
Organisme : National Natural Science Foundation of China
ID : 21702189
Organisme : Science and technology research and development plan joint fund
ID : 222301420042
Organisme : Zhengzhou University
ID : JC21253007
Informations de copyright
© 2024 The Authors. Advanced Science published by Wiley‐VCH GmbH.
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CCDC MQPhos‐1 (2284070) the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc. cam.ac.uk/structures.
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