Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

Claire L. Jarvis; Neyra M. Jemal; Spencer Knapp; Daniel Seidel

doi:10.1039/C8OB01015C

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Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins†

Claire L. Jarvis,^a Neyra M. Jemal,^a Spencer Knapp

^a and Daniel Seidel

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA
E-mail: seidel@chem.ufl.edu

^b Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA

Abstract

A new preparation of δ-lactams is reported. In the presence of a Lewis acid promoter, alkoxyisocoumarins engage a range of N-aryl and N-alkyl imines to form δ-lactams with a pendent carboalkoxy substituent. A sulfonamide-thiourea catalyst enables the synthesis of these products in moderate to good enantioselectivities.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB01015C
Article type: Communication
Submitted: 01 May 2018
Accepted: 18 May 2018
First published: 25 May 2018

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Org. Biomol. Chem., 2018,16, 4231-4235

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Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

C. L. Jarvis, N. M. Jemal, S. Knapp and D. Seidel, Org. Biomol. Chem., 2018, 16, 4231 DOI: 10.1039/C8OB01015C

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Organic & Biomolecular Chemistry

Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins†

Abstract

Supplementary files

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Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins

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