Novel Radical Reaction of Phenylsulfonyl Oxime Ethers. A Free Radical Acylation Approach

Kim, Sunggak; Lee, Ill Young; Yoon, Joo‐Yong; Oh, Dong‐Hwa

doi:10.1021/ja9600993

Cited by 130 publications

(42 citation statements)

References 38 publications

(12 reference statements)

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“…[23][24][25] In contrast, the recently described intermolecular acylation of alkyl radicals by acyl selenides and sulfides is very inefficient. 26 On treatment with tributylstannane and a radical initiator, acyl selenides 27,28 provide convenient sources of acyl radicals, 29 as do certain classes of acyl sulfide. [30][31][32] Alternatively, acyl tellurides 33 and acylcobalt(III) 34 derivatives can provide acyl radicals on white light photolysis.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of β-(Acyloxy)alkyl and β-(Phosphatoxy)alkyl Radicals and Related Species: Radical and Radical Ionic Migrations and Fragmentations of Carbon−Oxygen Bonds

et al. 1997

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ContentsI. Introduction 3273 II. Rearrangements 3275 A. β-(Acyloxy)alkyl Rearrangement 3275 1. Esters 3275 2. Lactones 3280 3. Thiocarbonyl Esters 3280 B. β-(Phosphatoxy)alkyl Rearrangement 3282 C. β-(Nitroxy)alkyl and β-(Sulfonatoxy)alkyl Rearrangements 3285 D. (Acyloxyalkyl)silyl Radical Rearrangement 3285 III. Fragmentation Reactions 3286 A. β-(Acyloxy)alkyl Radicals and Their Thiocarbonyl Analogues 3286 B. β-(Phosphatoxy)alkyl Radicals 3288 1. Anaerobic Conditions 3288 2. Aerobic Conditions 3293 C. β-(Sulfonatoxy)alkyl and Related Radicals 3294 IV. Mechanism 3294 A. β-(Ester)alkyl Radicals Susceptible to Neither Rearrangement Nor Fragmentation 3294 B. Fragmentation Reactions 3295 C. Rearrangement Reactions 3295 1. Noncage Dissociative Pathways 3296 2. Stepwise Pathways via Five-Membered Cyclic Intermediate Radicals 3296 3. Use of Isotopic and Stereochemical Labeling as Probes of Mechanism 3296 4. Quantitative Structure Activity Relationships 3298 5. Computational Studies and ESR Considerations 3299 V. Overview of β-(Ester)alkyl Radical Reactions 3303 VI. Related Reactions Involving Radical C−O Bond Shift and Cleavage 3305 A. Rearrangement and Fragmentation of β-Hydroxyalkyl Radicals 3305 B. Schenck or Allylperoxy Radical Rearrangement 3307 C. β-(Vinyloxy)alkyl to 4-Ketobutyl Rearrangement 3308 VII. Acknowledgments 3309 VIII. References 3309 Scheme 6

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Section: Introductionmentioning

confidence: 99%

Chemistry of β-(Acyloxy)alkyl and β-(Phosphatoxy)alkyl Radicals and Related Species: Radical and Radical Ionic Migrations and Fragmentations of Carbon−Oxygen Bonds

et al. 1997

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“…These considerations led us to seek alternatives to triethylborane. Applying Kim's photolysis conditions [32] in the presence of InCl 3 , we found that ethyl and isopropyl addition to hydrazone 3a occurred in reasonable yield ( Table 7, Entries 1 and 2).…”

Section: Tin-mediated Addition Of Primary Radicalsmentioning

confidence: 94%

Chiral N‐Acylhydrazones: Versatile Imino Acceptors for Asymmetric Amine Synthesis

Friestad

2005

Eur J Org Chem

122

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Addition to C=N bonds with acyclic stereocontrol offers excellent potential for development of new carbon-carbon bond construction approaches to chiral amines. This review features the design and implementation of novel chiral Nacylhydrazones as versatile imino acceptors for addition of radicals and nucleophiles. The initial design was inspired by the goal of asymmetric radical addition to chiral C=N radical acceptors. The chiral N-acylhydrazones are prepared from commercially available materials by amination of 4-alkyl-2-oxazolidinones with NH 2 + equivalents to afford N-(amino) oxazolidinones, followed by condensation with aldehydes or ketones. These chiral N-acylhydrazones undergo addition reactions with various partners, including radicals, allylsilanes, allylindiums, silyl enol ethers, and hydride donors. The MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included.

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“…On a similar basis, sulfonyloximes (such as 57, Scheme 16), a useful class of radical acceptors introduced by Kim et al [35] can successfully take part in a 4-CR-DAAD strategy. [36] The nucleophilic acyl radical 28 ii, generated as above (Scheme 15), efficiently adds to oxime 57 to provide, after b-fragmentation of one of the sulfonyl groups, a monosulfonyl oxime 57 i.…”

Section: Four-and Five-component Radical Reactions 4-cr-daadmentioning

confidence: 99%

Radical and Radical–Ionic Multicomponent Processes

Godineau

Landais

2009

Chemistry A European J

175

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All in one pot! Radical, radical-ionic, and radical-organometallic MCR are highly convergent processes, representing a useful pathway to molecular and structural diversity (see scheme). This concept article highlights recent developments in the field and shows the potential of the strategy for the economical elaboration of various kinds of organic substrates.Progress in multicomponent reactions (MCRs) based on ionic and organometallic processes has recently allowed the synthesis, with high efficiency, of large collections of drug-like molecules. In contrast, MCRs based on cascade radical reactions appear to have attracted, so far, much less interest. This concept article highlights the latest progress in the field and underlines the potential of such an approach. The collected examples demonstrate that radical and radical-ionic MCRs are highly convergent processes leading to useful structural diversity.

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Novel Radical Reaction of Phenylsulfonyl Oxime Ethers. A Free Radical Acylation Approach

Cited by 130 publications

References 38 publications

Chemistry of β-(Acyloxy)alkyl and β-(Phosphatoxy)alkyl Radicals and Related Species: Radical and Radical Ionic Migrations and Fragmentations of Carbon−Oxygen Bonds

Chemistry of β-(Acyloxy)alkyl and β-(Phosphatoxy)alkyl Radicals and Related Species: Radical and Radical Ionic Migrations and Fragmentations of Carbon−Oxygen Bonds

Chiral N‐Acylhydrazones: Versatile Imino Acceptors for Asymmetric Amine Synthesis

Radical and Radical–Ionic Multicomponent Processes

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