Organic Letters
Organic Letters
3 years ago

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
Q. Nhu N. Nguyen, Stephen W. Laws, Lucas C. Moore, Michael J. Di Maso, Dean J. Tantillo, Jared T. Shaw
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00468

DOI: 10.1021/acs.orglett.7b00468

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