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

doi:10.1021/acs.orglett.1c00711

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 journal › Article (Academic Journal) › peer-review

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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 language	English
Pages (from-to)	3038-3042
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	8
Early online date	6 Apr 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00711
Publication status	Published - 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.

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© 2021 American Chemical Society.

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at https://pubs.acs.org/doi/full/10.1021/acs.orglett.1c00711 . Please refer to any applicable terms of use of the publisher.
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Exploitation of highly strained rings in the development of photoredox-catalysed transformations
White, D. H. (Author), Aggarwal, V. K. (Supervisor) & Willis, C. L. (Supervisor), 9 May 2023
Student thesis: Doctoral Thesis › Doctor of Philosophy (PhD)

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

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.",

author = "White, {Dawn H.} and Adam Noble and Booker-Milburn, {Kevin I.} and Aggarwal, {Varinder K.}",

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: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c00711",

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pages = "3038--3042",

journal = "Organic Letters",

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T1 - Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins

AU - White, Dawn H.

AU - Noble, Adam

AU - Booker-Milburn, Kevin I.

AU - Aggarwal, Varinder K.

N1 - 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.

PY - 2021/4/16

Y1 - 2021/4/16

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.1c00711

DO - 10.1021/acs.orglett.1c00711

M3 - Article (Academic Journal)

C2 - 33821661

SN - 1523-7060

VL - 23

SP - 3038

EP - 3042

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

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

Abstract

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Student theses

Exploitation of highly strained rings in the development of photoredox-catalysed transformations

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