Synthesis of thiomorpholin‐3‐ones by a gold‐catalysed oxidative cyclisation‐rearrangement cascade from ynamides

Thomas Baker; Paul Davies

doi:10.1002/ejoc.201900603

Synthesis of thiomorpholin‐3‐ones by a gold‐catalysed oxidative cyclisation‐rearrangement cascade from ynamides

Thomas Baker, Paul Davies

Chemistry

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209 Downloads (Pure)

Abstract

A gold‐catalyzed oxidative N‐cyclisation strategy allows for the preparation of α‐aryl thiomorpholin‐3‐ones from readily assembled ynamides bearing tethered thioethers. A cascade of oxidation, cyclisation and then [2,3]‐ or [1,2]‐sigmatropic rearrangement of the resulting sulfonium ylide proceeds under mild reaction conditions. Cyclisation and intermolecular oxidation are in competition at two different stages of the reaction. The required switch in selectivity between these processes can be managed by combining pyridine N‐oxide oxidant with an IPrAuCl‐derived catalyst.

Original language	English
Pages (from-to)	5201-5204
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	31-32
Early online date	24 Jun 2019
DOIs	https://doi.org/10.1002/ejoc.201900603
Publication status	Published - 19 Aug 2019

Keywords

Cyclisation
Gold
Nitrogen heterocycles
Oxidation
Ynamide

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201900603Licence: None: All rights reserved

Baker_&_Davies_Synthesis_of_thiomorpholin_3_ones_European_Journal_of_Organic_Chemistry_2019
This is the peer reviewed version of the following article: Baker, T. and Davies, P. W. (2019), Synthesis of Thiomorpholin‐3‐ones by a Gold‐Catalysed Oxidative Cyclisation‐Rearrangement Cascade from Ynamides. Eur. J. Org. Chem., 2019: 5201-5204, which has been published in final form at https://doi.org/10.1002/ejoc.201900603. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Accepted author manuscript, 850 KBLicence: None: All rights reserved

https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201900603Licence: None: All rights reserved

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abstract = "A gold‐catalyzed oxidative N‐cyclisation strategy allows for the preparation of α‐aryl thiomorpholin‐3‐ones from readily assembled ynamides bearing tethered thioethers. A cascade of oxidation, cyclisation and then [2,3]‐ or [1,2]‐sigmatropic rearrangement of the resulting sulfonium ylide proceeds under mild reaction conditions. Cyclisation and intermolecular oxidation are in competition at two different stages of the reaction. The required switch in selectivity between these processes can be managed by combining pyridine N‐oxide oxidant with an IPrAuCl‐derived catalyst.",

keywords = "Cyclisation, Gold, Nitrogen heterocycles, Oxidation, Ynamide",

author = "Thomas Baker and Paul Davies",

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N2 - A gold‐catalyzed oxidative N‐cyclisation strategy allows for the preparation of α‐aryl thiomorpholin‐3‐ones from readily assembled ynamides bearing tethered thioethers. A cascade of oxidation, cyclisation and then [2,3]‐ or [1,2]‐sigmatropic rearrangement of the resulting sulfonium ylide proceeds under mild reaction conditions. Cyclisation and intermolecular oxidation are in competition at two different stages of the reaction. The required switch in selectivity between these processes can be managed by combining pyridine N‐oxide oxidant with an IPrAuCl‐derived catalyst.

AB - A gold‐catalyzed oxidative N‐cyclisation strategy allows for the preparation of α‐aryl thiomorpholin‐3‐ones from readily assembled ynamides bearing tethered thioethers. A cascade of oxidation, cyclisation and then [2,3]‐ or [1,2]‐sigmatropic rearrangement of the resulting sulfonium ylide proceeds under mild reaction conditions. Cyclisation and intermolecular oxidation are in competition at two different stages of the reaction. The required switch in selectivity between these processes can be managed by combining pyridine N‐oxide oxidant with an IPrAuCl‐derived catalyst.

KW - Cyclisation

KW - Gold

KW - Nitrogen heterocycles

KW - Oxidation

KW - Ynamide

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 31-32

ER -

Synthesis of thiomorpholin‐3‐ones by a gold‐catalysed oxidative cyclisation‐rearrangement cascade from ynamides

Abstract

Keywords

ASJC Scopus subject areas

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