Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins

Dawn H. White, Adam Noble, Kevin I. Booker-Milburn, Varinder K. Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

Abstract

A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.
Original languageEnglish
Pages (from-to)3038-3042
Number of pages5
JournalOrganic Letters
Volume23
Issue number8
Early online date6 Apr 2021
DOIs
Publication statusPublished - 16 Apr 2021

Bibliographical note

Funding Information:
We acknowledge the EPSRC (DTA award) for funding. We thank Dr. Natalie Pridmore (University of Bristol) for X-ray crystallography analysis and Sayad Doobary (University of Bristol) and Mark Deeprose (University of Bristol) for assistance with conducting cyclic voltammetry experiments.

Publisher Copyright:
© 2021 American Chemical Society.

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