Asymmetric Synthesis with Hypervalent Iodine Reagents

Kumar, Ravi; Wirth, Thomas

doi:10.1007/128_2015_639

Cited by 45 publications

(15 citation statements)

References 88 publications

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“…The most promising path to enantiomerically enriched iodocyclocarbamation products would seem to be through an eventual application of methodology involving chiral hypervalent iodine catalysts. The pioneering and ongoing work in this area by Denmark, Wirth, and Muñiz, among others, would seem to have considerable potential as a solution to this problem …”

Section: Discussionmentioning

confidence: 99%

The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method

et al. 2020

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3-Aryl- and 3-heteroaryloxazolidin-2-ones, by virtue of the diverse pharmacologic activities exhibited by them after subtle changes to their appended substituents, are becoming increasingly important and should be considered privileged chemical structures. The iodocyclocarbamation reaction has been extensively used to make many 3-alkyl-5-(halomethyl)oxazolidin-2-ones, but the corresponding aromatic congeners have been relatively underexplored. We suggest that racemic 3-aryl- and 3-heteroaryl-5-(iodomethyl)oxazolidin-2-ones, readily prepared by the iodocyclocarbamation reaction of N-allylated N-aryl or N-heteroaryl carbamates, may be useful intermediates for the rapid preparation of potential lead compounds with biological activity. We exemplify this point by using this approach to prepare racemic linezolid, an antibacterial agent. Herein, we report the results of our systematic investigation into the scope and limitations of this process and have identified some distinguishing characteristics within the aryl/heteroaryl series. We also describe the first preparation of 3-aryloxazolidin-2-ones bearing new functionalized C-5 substituents derived from conjugated 1,3-dienyl and cumulated 1,2-dienyl carbamate precursors. Finally, we describe the utility of the iodocyclocarbamation reaction for making six-membered tetrahydro-3-aryl-1,3-oxazin-2-ones.

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Section: Discussionmentioning

confidence: 99%

The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method

et al. 2020

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“…Aside from transition metal chemistry, hypervalent iodine itself has the aforementioned properties suitable for application in a diverse range of organic transformations. Consequently, over the past two decades, there have been several general reviews [1,2,3,4,5,6,7,8,9,10], books and book chapters [11,12,13], and specialized reviews [14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29] in this regard. In this review, we hence focus on progress and developments that have taken place in the past 10 years in the field of alkene difunctionalization such as diamination, aminofunctionalization, diacetoxylation, oxyfunctionalization, and dihalogenation reactions.…”

Section: Introductionmentioning

confidence: 99%

Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years

2019

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Hypervalent iodine reagents are of considerable relevance in organic chemistry as they can provide a complementary reaction strategy to the use of traditional transition metal chemistry. Over the past two decades, there have been an increasing number of applications including stoichiometric oxidation and catalytic asymmetric variations. This review outlines the main advances in the past 10 years in regard to alkene heterofunctionalization chemistry using achiral and chiral hypervalent iodine reagents and catalysts.

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“…As a consequence, the development of a transition-metal-free and environmentally benign synthetic protocol for N -heterocycles is highly desirable . Hypervalent iodine reagents have been identified as a useful alternative to common transition metals . Their particular appeal stems from their broad scope in general oxidation chemistry combined with the fact that their use is not hampered by the occurrence of residual metal contamination.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of Bromo-N-heterocycles through Dibromohydantoin-Promoted Tandem C–H Amination/Bromination

Gao

Jing

et al. 2019

J. Org. Chem.

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Herein, we report a metal-free radical tandem C–H amination and bromination reaction with dibromohydantoin (DBH) as both the amination and bromination reagents and water as the main solvent. The reaction involves in intramolecular C–H amination and electrophilic bromination using cheap commercially available DBH. The products represent heterocyclic building blocks, readily modifiable by classical cross-coupling reactions.

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Asymmetric Synthesis with Hypervalent Iodine Reagents

Abstract: This chapter describes recent developments in stereoselective synthesis using hypervalent iodine reagents.

Cited by 45 publications

References 88 publications

The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method

The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method

Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years

Syntheses of Bromo-N-heterocycles through Dibromohydantoin-Promoted Tandem C–H Amination/Bromination

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