Regio- and diastereoselective formation of 1,2-azidohydroperoxides by photooxygenation of alkenes in the presence of azide anions

Griesbeck, Axel G.; Hundertmark, Thomas; Steinwascher, Jörg

doi:10.1016/0040-4039(96)01932-6

Cited by 20 publications

(6 citation statements)

References 37 publications

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“…Griesbeck and co-workers have explored a unique alkene difunctionalization reaction in a series of investigations on azidohydroperoxidation facilitated by PET. − In an initial report, Rhodamine B ( RhBH-Cl ) was utilized as a photoredox catalyst in the transformation along with sodium azide (NaN 3 ) under aerobic conditions, which yielded a mixture of alcohols 168.3 and hydroperoxides 168.2 as products (Scheme ). The crude photolysis mixtures were treated with sodium sulfite (Na 2 SO 3 ) to give the alcohols 168.4 – 168.7 in greater than 90% yield.…”

Section: Rhodaminesmentioning

confidence: 99%

Organic Photoredox Catalysis

2016

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In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.

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Section: Rhodaminesmentioning

confidence: 99%

Organic Photoredox Catalysis

2016

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“…Photooxygenation in the presence of azide anions leads to difunctionalized products which can derive either from an azide trapping reaction of cyclic peroxidic intermediates or from an oxygen trapping reaction of intermediary a-azido carbon radicals. [1][2][3] The resulting 2-azidohydroperoxides have seldom been isolated and are usually reduced to the corresponding azido-or aminoalcohols. 4 Recent investigation by Workentin et al showed that azidyl radicals are produced under photoinduced electron transfer (PET) conditions and these highly reactive azidyl radicals readily add to nucleophilic alkenes.…”

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confidence: 99%

Azidohydroperoxidation of pinenes: stereoselectivity pattern and the first X-ray structure of a 2-azidohydroperoxide

et al. 2000

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“…Monoterpenoid azides 21 and 22 were prepared by photooxygenation in the presence of sodium azide of the corresponding olefins (+)-limonene and (−)-α-pinene and subsequent reduction, with sodium sulfite, of the hydroperoxy azide intermediates (Table ) …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Highly Functionalized Chiral Nitriles by Radical Fragmentation of β-Hydroxy Azides. Convenient Transformation of Aldononitriles into 1,4- and 1,5-Iminoalditols

et al. 2004

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The synthesis of highly functionalized nitriles by an alkoxyl radical fragmentation of cyclic beta-hydroxy azides is described. The alkoxyl radicals were generated by reaction of the alcohols with (diacetoxyiodo)benzene and iodine under mild conditions compatible with the presence of sensitive substituents and the protective groups most frequently used in carbohydrate chemistry. To explore the scope and limitations of this methodology, experiments were carried out using a variety of beta-hydroxy azides of the carbohydrate (1-6, 33, and 41), monoterpenoid (21 and 22), and steroid (23-25) families of natural products. Of special interest are the aldopentonitriles (15-18, 34, and 42) and aldotetrononitriles (19 and 20) synthesized from the corresponding 2-azido-2-deoxycarbohydrates. To demonstrate the versatility of these aldononitriles as chiral synthons, 1,4-imino-1-deoxysugar (37) and 1,5-imino-1-deoxysugar (43) analogues of the polyhydroxypyrrolidine and -piperidine types were prepared.

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Regio- and diastereoselective formation of 1,2-azidohydroperoxides by photooxygenation of alkenes in the presence of azide anions

Cited by 20 publications

References 37 publications

Organic Photoredox Catalysis

Organic Photoredox Catalysis

Azidohydroperoxidation of pinenes: stereoselectivity pattern and the first X-ray structure of a 2-azidohydroperoxide

Synthesis of Highly Functionalized Chiral Nitriles by Radical Fragmentation of β-Hydroxy Azides. Convenient Transformation of Aldononitriles into 1,4- and 1,5-Iminoalditols

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