Thermal fragmentation of sulfoximines of N-aminooxazolidones. A novel olefin synthesis

White, James D.; Kim, Moon-Geu

doi:10.1016/s0040-4039(01)91907-0

Cited by 14 publications

(6 citation statements)

References 10 publications

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“…In the reaction of styrene oxide, the attack by hydrazine occurs from the less hindered side of the epoxide, resulting in a 2 : 1 mixture of 2-hydrazino-1-phenylethanol (7) and 2-hydrazino-2-phenylethanol (8) [28,29]. Hydrazinoalcohol 10 was detected as the only regioisomer in the hydrazinolysis of the chiral epoxide 9, and the unstable compound 10 was promptly transformed into (3S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylic acid (11), which is an unusual amino acid constituent of luzopeptin A, an antitumor antibiotic depsipeptide, isolated from Actinomadura luzonensis [25] (Scheme 3).…”

Section: Epoxide Ring-openings With Hydrazine Derivatives (Methods A)mentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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Hydrazinoalcohols are versatile di-or trifunctional compounds with wide-ranging possibilities for application in organic synthesis. Numerous methods have been devised for the preparation of this family of compounds in recent decades. This review discusses the main pathways for the synthesis of hydrazinoalcohol derivatives, including epoxide ring-openings and nucleophilic substitutions by hydrazines, addition reactions to hydroxyhydrazones, hydrazine additions to olefinic bonds, electrophilic C-and N-amination reactions, cycloadditions, reductions of N-nitroso aminoalcohols and some unique procedures. The latest developments in these fields, involving both conventional and enzymatic catalytic methods of synthetic organic chemistry, allow the highly regio-, stereo-and enantioselective preparation of hydrazinoalcohol derivatives.

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Section: Epoxide Ring-openings With Hydrazine Derivatives (Methods A)mentioning

confidence: 99%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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“…Famous examples are iminations involving TsN 3 77, 78 (Scheme 1, Path E) or various N-amino substituted compounds (Scheme 1, Path H). [85][86][87][88][89][90][91] An interesting application of this chemistry, going beyond its immediate importance as a source of (optically active) sulfoximines is a thermal fragmentation reaction yielding sterically congested alkenes (Scheme 3). 87…”

Section: From Sulfoxides and Sulfiliminesmentioning

confidence: 99%

Sulfoximines: Structures, Properties and Synthetic Applications

2000

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This review presents a comprehensive treatment of sulfoximine chemistry particularly emphasising synthetic developments and structural work after 1985. Following a brief introduction, the structures and properties of sulfoximines and metallated sulfoximines are discussed. The second section deals with the preparation of sulfoximines emphasising new methods. The main part of the review is concerned with reactions of sulfoximines. The material in this section is organised based on the reactivity pattern displayed by the various sulfoximines. Therefore they are grouped roughly into three classes of compounds. The first group of sulfoximines comprises compounds acting as C-nucleophiles, the second one contains electrophilic sulfoximines and the last group is made up of sulfoximines being useful as (chiral) ligands particularly for transition metals. Finally the ability of sulfoximines to act as "chiral chemical chameleons" and their rôle in biological and medicinal chemistry is briefly discussed.

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“…It might be noted that at least one example of nonstereospecificity in a three-membered ring analog (diphenylethyleneazamine) of the above systems has been recorded (Carpino and Kirkley, 1970). The reaction plausibly is concerted (White and Kim, 1974;Kim and White, 1975). (28)].…”

Section: (16)mentioning

confidence: 99%

Cheletropic Reactions

Mock¹

1977

Organic Chemistry: A Series of Monographs

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Thermal fragmentation of sulfoximines of N-aminooxazolidones. A novel olefin synthesis

Cited by 14 publications

References 10 publications

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Sulfoximines: Structures, Properties and Synthetic Applications

Cheletropic Reactions

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