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

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.

Citation

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

Publication

Organic Letters

Status

Peer reviewed

DOI

https://doi.org/10.1021/acs.orglett.2c02170

ISSN

1523-7060

Type

Journal article

Rights

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.

Description

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.)].

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/25678