Ring Rearrangement of 1,3‐Azasilinyl‐4‐epoxides to Synthesize 2‐Silamorpolines by a Si−C Bond Migration/Oxidation Process

Zhou, Song; Tu, Xiaoyu; He, Yuanhang; L, Gao; Song, Zhen

doi:10.1002/ejoc.202200766

Cited by 2 publications

(1 citation statement)

References 53 publications

(16 reference statements)

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“…irane (see the Supporting Information for further details). 29 Under our conditions, the House-Meinwald rearrangement proceeded with low catalyst loading and we isolated 67% of 1-phenylcyclopentane carbaldehyde (2). In addition, we observed the formation of 2-phenyl cyclohexanone (3) and some dimerization products in very small amounts via GC-MS; however, we were not able to isolate these compounds.…”

Section: Cluster Synlettmentioning

confidence: 89%

Organocatalytic, Chemoselective, and Stereospecific House–Meinwald Rearrangement of Trisubstituted Epoxides

Schreiner,

Dressler,

Öhler

et al. 2023

Synlett

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We present a novel method for the chemoselective House-Meinwald rearrangement of trisubstituted epoxides under mild conditions with the use of simple perfluorinated disulfonimides as Brønsted acid catalysts. We isolated the α-quaternary aldehyde products in yields of 27-97% using catalyst loadings as low as 0.5 mol% on a scale of 1 mmol. In addition, we show the stereospecific rearrangement using an enantioenriched substrate, which makes this method suitable for applications in total synthesis of natural products.

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Section: Cluster Synlettmentioning

confidence: 89%

Organocatalytic, Chemoselective, and Stereospecific House–Meinwald Rearrangement of Trisubstituted Epoxides

Schreiner,

Dressler,

Öhler

et al. 2023

Synlett

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Yoshimura,

Zhdankin

2024

Chem. Rev.

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Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7−8 years, between 2016 and 2024.

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Ring Rearrangement of 1,3‐Azasilinyl‐4‐epoxides to Synthesize 2‐Silamorpolines by a Si−C Bond Migration/Oxidation Process

Abstract: PhI(OAc)2/CuI‐promoted ring rearrangement of 1,3‐azasilinyl‐4‐epoxides has been developed. The reaction proceeds by a Si−C bond migration/oxidation process, leading to structurally novel 2‐silamorpolines containing an aryl/aldehyde groups‐substituted quaternary carbon.

Cited by 2 publications

References 53 publications

Organocatalytic, Chemoselective, and Stereospecific House–Meinwald Rearrangement of Trisubstituted Epoxides

Organocatalytic, Chemoselective, and Stereospecific House–Meinwald Rearrangement of Trisubstituted Epoxides

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

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