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

doi:10.1021/acs.orglett.7b00468

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	2466-2469
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00468
State	Published - 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

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AU - Di Maso, Michael J.

AU - Nguyen, Q. Nhu N.

AU - Tantillo, Dean J.

AU - Shaw, Jared T.

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