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Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade

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journal contribution
posted on 18.09.2019, 14:29 by Mindaugas Šiaučiulis, Selma Sapmaz, Alexander P. Pulis, David J. Procter
A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, via an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a charge accelerated [3,3]-sigmatropic rearrangement.

Funding

We thank The University of Manchester (Lectureship to A. P. P.), EPSRC (PhD studentship to M. S. and Established Career Fellowship to D. J. P.), and Eli Lilly (PhD studentship to M. S.). All publication charges for this article have been paid for by the Royal Society of Chemistry

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Citation

Chemical Science, 2018, 9 (3), pp. 754-759

Author affiliation

/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry

Version

VoR (Version of Record)

Published in

Chemical Science

Publisher

Royal Society of Chemistry:

issn

2041-6520

eissn

2041-6539

Acceptance date

17/11/2017

Copyright date

2017

Available date

18/09/2019

Publisher version

https://pubs.rsc.org/en/content/articlelanding/2018/SC/C7SC04723A#!divAbstract

Notes

Electronic supplementary information (ESI) available: Full experimental details, NMR spectra, CCDC numbers for X-ray structures. CCDC 1570504, 1570698. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc04723a

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en

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