Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N–H‑Free 1,5-Benzothiazepines
An unprecedented formal [3 + 4] annulation of α,β-unsaturated acyl azoliums with 2-aminobenzenethiols has been utilized to synthesize enantioenriched N–H-free 1,5-benzothiazepines, which are recognized as privileged structures in numerous biologically active scaffolds. This protocol offers a rapid a...
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Veröffentlicht in: | Organic letters 2017-07, Vol.19 (13), p.3470-3473 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | An unprecedented formal [3 + 4] annulation of α,β-unsaturated acyl azoliums with 2-aminobenzenethiols has been utilized to synthesize enantioenriched N–H-free 1,5-benzothiazepines, which are recognized as privileged structures in numerous biologically active scaffolds. This protocol offers a rapid and direct pathway to access the target compounds with high enantioselectivities and has been applied in the concise synthesis of chiral drug (R)-thiazesim. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.7b01457 |