Umsetzungen von Δ5-steroidolefinen mit Pb(OAC)4-n(N3)n

Hugl, Herbert; Zbiral, E.

doi:10.1016/0040-4020(73)80090-0

Cited by 17 publications

(2 citation statements)

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“…Methodologies for the synthesis of ketonitriles include the Beckmann fragmentation of cyclic α-hydroxy oximes and the cleavage of trisubstituted cyclic olefins with (diacetoxyiodo)benzene (DIB)/(TMS)N 3 . Alternatively, Pb(OAc) 4 /(TMS)N 3 , CAN/NaN 3 , or photooxygenation in the presence of NaN 3 /Cu(OTf) 2 7 can achieve the same results. On the other hand, highly functionalized aldononitriles have found widespread applications as chiral synthons in the preparation of polyhydroxypiperidines (1,5-iminoalditols) and polyhydroxypyrrolidines (1,4-iminoalditols); the latter are glycosidase inhibitors .…”

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confidence: 93%

New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

Fan

et al. 2006

Org. Lett.

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confidence: 93%

New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

Fan

et al. 2006

Org. Lett.

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“…(1 S ,3 S ) - (3-Acetyl-2,2-dimethylcyclobutyl)acetonitrile (27). The product isolated by chromatography (hexanes−EtOAc, 85:15) has already been partially described 2b. In our hands, it was obtained as an oil (82%): [α] D −97 ( c 0.196) (lit 2b…”

Section: Methodsmentioning

confidence: 75%

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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