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

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

Research output: Contribution to journalArticle

5 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2466-2469
Number of pages4
JournalOrganic Letters
Volume19
Issue number10
DOIs
StatePublished - May 19 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Laws, S. W., Moore, L. C., Di Maso, M. J., Nguyen, Q. N. N., Tantillo, D. J., & Shaw, J. T. (2017). Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides. Organic Letters, 19(10), 2466-2469. https://doi.org/10.1021/acs.orglett.7b00468