Stereoselective synthesis of cyclobutanes by contraction of pyrrolidines

Hui, C., Brieger, L., Strohmann, C. and Antonchick, A.P. ORCID: 0000-0003-0435-9443, 2021. Stereoselective synthesis of cyclobutanes by contraction of pyrrolidines. Journal of the American Chemical Society, 143 (45), pp. 18864-18870. ISSN 0002-7863

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Abstract

Here we report a contractive synthesis of multisubstituted cyclobutanes containing multiple stereocenters from readily accessible pyrrolidines using iodonitrene chemistry. Mediated by a nitrogen extrusion process, the stereospecific synthesis of cyclobutanes involves a radical pathway. Unprecedented unsymmetrical spirocyclobutanes were prepared successfully, and a concise, formal synthesis of the cytotoxic natural product piperarborenine B is reported.

Item Type: Journal article
Publication Title: Journal of the American Chemical Society
Creators: Hui, C., Brieger, L., Strohmann, C. and Antonchick, A.P.
Publisher: American Chemical Society (ACS)
Date: 17 November 2021
Volume: 143
Number: 45
ISSN: 0002-7863
Identifiers:
NumberType
10.1021/jacs.1c10175DOI
1497166Other
Rights: © 2021 The Authors. Published by American Chemical Society. Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/pag...right/permissions.html. This content is freely available under simple legal terms because of Creative Commons, a non-profit that survives on donations.
Divisions: Schools > School of Science and Technology
Record created by: Linda Sullivan
Date Added: 22 Nov 2021 14:00
Last Modified: 22 Nov 2021 14:00
URI: http://irep.ntu.ac.uk/id/eprint/44917

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