Isothiourea-catalysed enantioselective radical conjugate addition under batch and flow conditions

Roberto del Río-Rodríguez; Matthew Westwood; Marina Sicignano; Martin Juhl; Jose A. Fernández-Salas; José  Alemán; Andrew D. Smith

doi:10.1039/D2CC02432B

Isothiourea-catalysed enantioselective radical conjugate addition under batch and flow conditions

Roberto del Río-Rodríguez, Matthew Westwood, Marina Sicignano, Martin Juhl, Jose A. Fernández-Salas, José Alemán^*, Andrew D. Smith^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The photocatalytic generation of α-amino radicals is combined with chiral isothiourea derived α,β-unsaturated acyl ammonium intermediates. The reaction proceeds via a [3+2] radical-polar crossover mechanism to generate γ-lactams in good yields and enantioselectivities. The enantioselective radical conjugate addition was carried out under batch and flow conditions.

Original language	English
Pages (from-to)	7277-7280
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	52
Early online date	25 May 2022
DOIs	https://doi.org/10.1039/D2CC02432B
Publication status	Published - 4 Jul 2022

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10.1039/D2CC02432BLicence: CC BY

Rio-Rodriguez_2022_CC_Enantioselective_CC
Copyright © 2022 The Author(s). Open Access. This article is licensed under aCreative Commons Attribution 3.0 Unported Licence.
Final published version, 2.86 MBLicence: CC BY

data underpinning "Isothiourea-Catalysed Enantioselective Radical Conjugate Addition under Batch and Flow Conditions"
Smith, A. D. (Creator) & Westwood, M. (Creator), University of St Andrews, 27 May 2022
DOI: 10.17630/2522a5e8-3d9f-4b24-8aec-46c8a455b394
Dataset

File

Novel isothiourea catalysts and reactivity
Westwood, M. (Author), Smith, A. D. (Supervisor), 13 Jun 2024
Student thesis: Doctoral Thesis (PhD)

Cite this

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title = "Isothiourea-catalysed enantioselective radical conjugate addition under batch and flow conditions",

abstract = "The photocatalytic generation of α-amino radicals is combined with chiral isothiourea derived α,β-unsaturated acyl ammonium intermediates. The reaction proceeds via a [3+2] radical-polar crossover mechanism to generate γ-lactams in good yields and enantioselectivities. The enantioselective radical conjugate addition was carried out under batch and flow conditions.",

author = "{del R{\'i}o-Rodr{\'i}guez}, Roberto and Matthew Westwood and Marina Sicignano and Martin Juhl and Fern{\'a}ndez-Salas, {Jose A.} and Jos{\'e} Alem{\'a}n and Smith, {Andrew D.}",

note = "Financial support was provided by the Spanish Government (RTI2018-095038-B-I00), “Comunidad de Madrid” for European Structural Funds (S2018/NMT-4367) and proyectos sinergicos I+D (Y2020/NMT-6469). J. A. F.-S. thanks the Spanish Government for a Ram{\'o}n y Cajal contract. The research leading to these results has received funding from the EaSI-CAT centre for Doctoral Training (M.T.W) and Carlsberg Foundation (M.J.).",

year = "2022",

month = jul,

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doi = "10.1039/D2CC02432B",

language = "English",

volume = "58",

pages = "7277--7280",

journal = "Chemical Communications",

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T1 - Isothiourea-catalysed enantioselective radical conjugate addition under batch and flow conditions

AU - del Río-Rodríguez, Roberto

AU - Westwood, Matthew

AU - Sicignano, Marina

AU - Juhl, Martin

AU - Fernández-Salas, Jose A.

AU - Alemán, José

AU - Smith, Andrew D.

N1 - Financial support was provided by the Spanish Government (RTI2018-095038-B-I00), “Comunidad de Madrid” for European Structural Funds (S2018/NMT-4367) and proyectos sinergicos I+D (Y2020/NMT-6469). J. A. F.-S. thanks the Spanish Government for a Ramón y Cajal contract. The research leading to these results has received funding from the EaSI-CAT centre for Doctoral Training (M.T.W) and Carlsberg Foundation (M.J.).

PY - 2022/7/4

Y1 - 2022/7/4

N2 - The photocatalytic generation of α-amino radicals is combined with chiral isothiourea derived α,β-unsaturated acyl ammonium intermediates. The reaction proceeds via a [3+2] radical-polar crossover mechanism to generate γ-lactams in good yields and enantioselectivities. The enantioselective radical conjugate addition was carried out under batch and flow conditions.

AB - The photocatalytic generation of α-amino radicals is combined with chiral isothiourea derived α,β-unsaturated acyl ammonium intermediates. The reaction proceeds via a [3+2] radical-polar crossover mechanism to generate γ-lactams in good yields and enantioselectivities. The enantioselective radical conjugate addition was carried out under batch and flow conditions.

U2 - 10.1039/D2CC02432B

DO - 10.1039/D2CC02432B

M3 - Article

SN - 1359-7345

VL - 58

SP - 7277

EP - 7280

JO - Chemical Communications

JF - Chemical Communications

IS - 52

ER -

Isothiourea-catalysed enantioselective radical conjugate addition under batch and flow conditions

Abstract

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Datasets

data underpinning "Isothiourea-Catalysed Enantioselective Radical Conjugate Addition under Batch and Flow Conditions"

Student theses

Novel isothiourea catalysts and reactivity

Cite this