Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins
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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.
Abdelhamid , Y , Kasten , K , Dunne , J , Hartley , W , Young , C M , Cordes , D B , Slawin , A M Z , Ng , S & Smith , A D 2022 , ' Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins ' , Organic Letters , vol. Articles ASAP . https://doi.org/10.1021/acs.orglett.2c02170
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.
DescriptionThe 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.)].
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