Use of the Nosyl Group as a Functional Protecting Group in Applications of a Michael/Smiles Tandem Process

Coulibali, Siomenan; Godou, Timothé; Canesi, Sylvain

doi:10.1021/acs.orglett.6b02105

Cited by 39 publications

(18 citation statements)

References 66 publications

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“…Canesi recently demonstrated the use of nosyl groups in several intramolecular Michael addition/Truce–Smiles rearrangement reactions . Intramolecular addition of the nosyl‐amine in 103 to the enone led to a Truce–Smiles rearrangement; however, the final product 104 was a result of a retro‐Michael and second 1,4‐addition of the amine (Scheme a).…”

Section: Two‐electron Smiles Rearrangementmentioning

confidence: 99%

Modern Aspects of the Smiles Rearrangement

Holden

Greaney

2017

Chemistry A European J

165

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The Smiles rearrangement is an intramolecular S Ar reaction, breaking a C-X single bond and forming a new C-X or C-C bond though ipso substitution. Its vast scope, in terms of nucleophile, leaving group, and ring-size of the transition state, make it a powerful tool for arene functionalization, as it can be employed strategically to switch easily-forged bonds with more difficult connections that would be challenging to realize in the intermolecular mode. The reaction has received significantly renewed attention in recent years, as advances in areas such as arene C-X bond formation and radical generation have been harnessed for new arene syntheses through Smiles chemistry. In addition, new reaction modes have been discovered, such as the Clayden rearrangement of lithiated ureas, creating innovative applications for Smiles rearrangements in asymmetric arylation. This Minireview will discuss advances in these areas in the recent literature, covering both two-electron, polar Smiles rearrangements along with single-electron radical transformations.

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Section: Two‐electron Smiles Rearrangementmentioning

confidence: 99%

Modern Aspects of the Smiles Rearrangement

Holden

Greaney

2017

Chemistry A European J

165

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“…To verify the feasibility of a Michael-Smiles tandem process to produce heterocycles such as indoles or indolines under mild conditions, 57 we prepared several dienones containing a Fukuyama sulfonamide 58 on the lateral chain using hyperlavent iodine chemistry. We chose acetonitrile as a solvent for this reaction because it is polar and relatively nontoxic, and Cs 2 CO 3 as an inorganic base.…”

Section: Syn Lettmentioning

confidence: 99%

Rapid Formation of Advanced Scaffolds from Phenols and Anilines

Canesi

2018

Synlett

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This article is an account of our efforts over the last decade to functionalize phenols and anilines at any position and to use these compounds to generate substituted aromatic systems and advanced unsaturated cyclohexanone moieties, enabling the rapid formation of complex structures. Total syntheses of numerous natural products involving such intermediates were achieved.1 Introduction2 ortho-Functionalization of Phenols and Aniline Derivatives Mediated by Iodanes (III) and Synthesis of Panacene2.1 Cross-Coupling with Aniline Derivatives2.2 Dearomative Cycloaddition of Arenes and Heteroarenes2.3 Total Synthesis of Panacene3 meta-Functionalization of Aniline Derivatives and Synthesis of Erysotramidine3.1 meta-Functionalization of Aniline Derivatives3.2 Total Synthesis of Erysotramidine4 para-Functionalization of Phenols and Applications in Total Synthesis4.1 Bimolecular Approach Mediated by Protecting Groups4.2 ipso-Rearrangement4.3 Oxidative Alkyl Shift4.4 Oxidative Prins-Pinacol Rearrangement4.5 Oxidative Prins-Type Reaction4.6 Total Synthesis of (–)-Fortucine4.7 Total Synthesis of Isostrychnine4.8 Total Synthesis of (–)-Strychnopivotine5 Development of a Functional Protecting Group

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“…To this end, we developed a methodology enabling the formation of functionalized scaffolds 3 mediated by a Michael−Smiles tandem process. 7 In this paper we describe a new application of this approach on a halogenated enone to develop an arylative cyclopropanation strategy, Scheme 1.…”

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confidence: 98%

A Stereoselective Arylative-Cyclopropanation Process

et al. 2017

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A new stereoselective arylative cyclopropanation process involving treatment of halogenated dienone systems in the presence of a Michael donor containing a nitro-aryl-sulfone has been developed. This transformation enables production of an arylated cyclopropane under mild conditions and occurs via a Michael-Smiles ring closure cascade process, reflecting the concepts of green chemistry and atom economy.

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Use of the Nosyl Group as a Functional Protecting Group in Applications of a Michael/Smiles Tandem Process

Cited by 39 publications

References 66 publications

Modern Aspects of the Smiles Rearrangement

Modern Aspects of the Smiles Rearrangement

Rapid Formation of Advanced Scaffolds from Phenols and Anilines

A Stereoselective Arylative-Cyclopropanation Process

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