Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N‑Sulfonyl Imines and Cyclic Anhydrides

Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N‑Sulfonyl Imines and Cyclic Anhydrides

A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures...

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Veröffentlicht in:Organic letters 2017-05, Vol.19 (10), p.2466-2469
Hauptverfasser: Laws, Stephen W, Moore, Lucas C, Di Maso, Michael J, Nguyen, Q. Nhu N, Tantillo, Dean J, Shaw, Jared T
Format: Artikel
Sprache:eng
Schlagworte:
aldehydes
anhydrides
chemical reactions
chemical structure
diastereoselectivity
imines
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Beschreibung
Zusammenfassung:A diastereoselective base-catalyzed Mannich reaction of cyclic, enolizable anhydrides and N-sulfonyl imines for the synthesis of δ-lactams is reported. This anhydride Mannich reaction tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed product epimerization pathway ensures high anti diastereoselectivity in aryl and achiral enolizable imines.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b00468