Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins

Yusra Abdelhamid; Kevin Kasten; Joanne Dunne; Will Hartley; Claire M. Young; David B. Cordes; Alexandra M. Z. Slawin; Sean Ng; Andrew D. Smith

doi:10.1021/acs.orglett.2c02170

Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins

Yusra Abdelhamid, Kevin Kasten, Joanne Dunne, Will Hartley, Claire M. Young, David B. Cordes, Alexandra M. Z. Slawin, Sean Ng, Andrew D. Smith^*

^*Corresponding author for this work

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

Abstract

Enantioselective [2+2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N alkyl isatins gives spirocyclic β-lactones. In situ ring-opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er.

Original language	English
Number of pages	6
Journal	Organic Letters
Volume	Articles ASAP
Early online date	18 Jul 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c02170
Publication status	E-pub ahead of print - 18 Jul 2022

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10.1021/acs.orglett.2c02170Licence: CC BY

Abdelhamid_2022_OL_Isothiourea_CC
Copyright © 2022 The Authors. Published by American Chemical Society.This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 1.56 MBLicence: CC BY

Exploiting Chalcogen Bonding and Non: Exploiting Chalcogen Bonding and Non-Covalent Interactions in Isochalcogenourea Catalysis: Catalyst Preparation, Mechanistic Studies and Applications
Smith, A. D. (PI)
1/11/20 → 31/10/23
Project: Standard
Underpinning Mechanistic Studies: Underpinning Mechanistic Studies of NHC-Organocatalysis: A Breslow Intermediate Reactivity Scale
Smith, A. D. (PI)
EPSRC
1/04/19 → 31/12/22
Project: Standard
CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

data underpinning "Isothiourea-Catalyzed [2+2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins"
Smith, A. D. (Creator), Kasten, K. (Creator), Young, C. M. (Creator) & Slawin, A. M. Z. (Creator), University of St Andrews, 25 Jul 2022
DOI: 10.17630/40852daa-0199-41e9-afb0-600a47d25ab9
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@article{86cc21e4aad34752a96f1202b0db1169,

title = "Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins",

abstract = "Enantioselective [2+2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N alkyl isatins gives spirocyclic β-lactones. In situ ring-opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er. ",

author = "Yusra Abdelhamid and Kevin Kasten and Joanne Dunne and Will Hartley and Young, {Claire M.} and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Sean Ng and Smith, {Andrew D.}",

note = "The research leading to these results has received funding from the EPSRC (EP/S019359/1, C. Y.; EP/T023643/1, J. D.; K. K.) as well as Syngenta and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis [CRITICAT, EP/L016419/1 (W.C.H.)].",

year = "2022",

month = jul,

day = "18",

doi = "10.1021/acs.orglett.2c02170",

language = "English",

volume = "Articles ASAP",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

}

TY - JOUR

T1 - Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins

AU - Abdelhamid, Yusra

AU - Kasten, Kevin

AU - Dunne, Joanne

AU - Hartley, Will

AU - Young, Claire M.

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Ng, Sean

AU - Smith, Andrew D.

N1 - The research leading to these results has received funding from the EPSRC (EP/S019359/1, C. Y.; EP/T023643/1, J. D.; K. K.) as well as Syngenta and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis [CRITICAT, EP/L016419/1 (W.C.H.)].

PY - 2022/7/18

Y1 - 2022/7/18

N2 - Enantioselective [2+2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N alkyl isatins gives spirocyclic β-lactones. In situ ring-opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er.

AB - Enantioselective [2+2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N alkyl isatins gives spirocyclic β-lactones. In situ ring-opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er.

U2 - 10.1021/acs.orglett.2c02170

DO - 10.1021/acs.orglett.2c02170

M3 - Article

SN - 1523-7060

VL - Articles ASAP

JO - Organic Letters

JF - Organic Letters

ER -

Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins

Abstract

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Projects

Exploiting Chalcogen Bonding and Non: Exploiting Chalcogen Bonding and Non-Covalent Interactions in Isochalcogenourea Catalysis: Catalyst Preparation, Mechanistic Studies and Applications

Underpinning Mechanistic Studies: Underpinning Mechanistic Studies of NHC-Organocatalysis: A Breslow Intermediate Reactivity Scale

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Datasets

data underpinning "Isothiourea-Catalyzed [2+2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins"

Cite this