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 journal › Article

4 Citations (Scopus)

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

Fingerprint

Imines
Cycloaddition
Anhydrides
Cycloaddition Reaction
cycloaddition
anhydrides
imines
Mannich Bases
Lactams
aldehydes
Aldehydes
synthesis
products

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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

Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides. / Laws, Stephen W.; Moore, Lucas C.; Di Maso, Michael J.; Nguyen, Q. Nhu N.; Tantillo, Dean J.; Shaw, Jared T.

In: Organic Letters, Vol. 19, No. 10, 19.05.2017, p. 2466-2469.

Research output: Contribution to journal › Article

Laws, SW, Moore, LC, Di Maso, MJ, Nguyen, QNN, Tantillo, DJ & Shaw, JT 2017, 'Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides', Organic Letters, vol. 19, no. 10, pp. 2466-2469. https://doi.org/10.1021/acs.orglett.7b00468
Laws SW, Moore LC, Di Maso MJ, Nguyen QNN, Tantillo DJ, Shaw JT. Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides. Organic Letters. 2017 May 19;19(10):2466-2469. https://doi.org/10.1021/acs.orglett.7b00468
Laws, Stephen W. ; Moore, Lucas C. ; Di Maso, Michael J. ; Nguyen, Q. Nhu N. ; Tantillo, Dean J. ; Shaw, Jared T. / Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides. In: Organic Letters. 2017 ; Vol. 19, No. 10. pp. 2466-2469.
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