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

Author:
Laws, Stephen W., Moore, Lucas C., Di Maso, Michael J., Nguyen, Q. Nhu N., Tantillo, Dean J., Shaw, Jared T.
Source:
Organic letters 2017 v.19 no.10 pp. 2466-2469
ISSN:
1523-7052
Subject:
aldehydes, anhydrides, chemical reactions, chemical structure, diastereoselectivity, imines
Abstract:
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.
Agid:
5792829