Chiral Phosphoric Acid Catalyzed Kinetic Resolution of 2‐Amido Benzyl Alcohols: Asymmetric Synthesis of 4H‐3,1‐Benzoxazines

An efficient method for the asymmetric synthesis of 4H‐3,1‐benzoxazines was developed by kinetic resolution of 2‐amido benzyl alcohols using chiral phosphoric acid catalyzed intramolecular cyclizations. A broad range of benzyl alcohols (both secondary and tertiary alcohols) were kinetically resolved...

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Published inAngewandte Chemie Vol. 132; no. 6; pp. 2353 - 2357
Main Authors Rajkumar, Subramani, Tang, Mengyao, Yang, Xiaoyu
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 03.02.2020
Subjects
Alcohol
Alcohols
Alkohole
Asymmetric synthesis
Asymmetry
Benzoxazines
Benzyl alcohol
Biological activity
Chemical industry
Chemistry
Heterocyclen
Kinetische Racematspaltung
Modularity
Organokatalyse
Phosphoric acid
Reaktionsmechanismen
Sigma factor
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Summary:An efficient method for the asymmetric synthesis of 4H‐3,1‐benzoxazines was developed by kinetic resolution of 2‐amido benzyl alcohols using chiral phosphoric acid catalyzed intramolecular cyclizations. A broad range of benzyl alcohols (both secondary and tertiary alcohols) were kinetically resolved with high selectivities, with an s factor of up to 94. Mechanistic studies were performed to elucidate the mechanism of these reactions, wherein the amide moieties reacted as the electrophiles. Gram‐scale reaction and facile transformations of the chiral products demonstrate the potential of this method in asymmetric synthesis of biologically active chiral heterocycles. Ein praktischer Ansatz für die asymmetrische Synthese von 4H‐3,1‐Benzoxazinen basiert auf der kinetischen Racematspaltung von 2‐Amidobenzylalkoholen in Gegenwart einer chiralen Phosphorsäure (CPA). Die Methode erfasst einen breiten Substratbereich zeichnet sich durch eine exzellente kinetische Racematspaltung aus, mit einem s‐Faktor bis zu 94.
Bibliography:These authors contributed equally to this work.
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201913896