Hydroxyselanylation of acyloxycyclohex-3-enes

Sweeney, Joseph B.; Haughan, Alan F.; Knight, J. R.; Thobhani, Smita

doi:10.1016/j.tet.2006.12.035

Cited by 6 publications

(1 citation statement)

References 28 publications

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“…We then addressed regio- and diastereoselective selenohydroxylation of 24a to obtain 25a . Our initial attempt using N -phenylselenophthalimide (N-PSP) and CSA in CH 2 Cl 2 -containing water gave, after stirring for 2 h, hydroxy selenide 26b with undesired diastereoselectivity as the only detectable selenohydroxylation product along with 24b (desilylated form of starting material 24a ) (3:5 26b : 24b ) . Surprisingly, however, when the reaction time was prolonged to 40 h under otherwise identical conditions, reversal of diastereoselectivity took place, affording a 9:1 inseparable mixture of 25b (desilylated form of 25a ) and 26b in 70% yield .…”

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Synthesis of Strophasterols C, E, and F

Sato

Kuwahara

2020

Org. Lett.

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The synthesis of strophasterols C, E, and F has been accomplished from a 14,15-secoergostane derivative via a 1,3-dipolar cycloaddition of a nitrile oxide intermediate to simultaneously install an isolated cyclopentane ring and a C23 oxygen functionality in a diastereoselective manner and a regio- and diastereoselective selenohydroxylation of an olefinic intermediate under thermodynamic conditions. This synthesis also enabled the stereochemical confirmation of strophasterol C.

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Synthesis of Strophasterols C, E, and F

Sato

Kuwahara

2020

Org. Lett.

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Advances in Free Radical Reactions of Organoselenium and Organotellurium Compounds

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2011

Patai's Chemistry of Functional Groups

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Free radical reactions of organoselenium and tellurium compounds have been widely studied and exploited since the first two volumes of this series appeared. Alkyl aryl selenides and tellurides undergo alkyl C‐Se or C‐Te cleavage with stannanes or silanes to generate alkyl radicals that can be employed in reductions, allylations and both intermolecular and intramolecular additions to a large variety of unsaturated substrates, terminated by either hydrogen or arylchalcogen transfer. Selenoesters, telluroesters and related species generate acyl radicals that are useful in overall decarboxylations of carboxylic acids, and in addition and radical cyclization processes, including cascade reactions of polyenes to afford polycyclic products. Homolytic cleavage of diselenides and ditellurides produces selenyl and telluryl radicals that can be employed in additions to unsaturated acceptors, while the dichalcogenides themselves function as effective trapping agents for radicals produced in a variety of other ways, as from Barton thiohydroxamates. Selenols are efficient hydrogen donors that are of importance in kinetic studies of radical processes. When selenium and tellurium are joined to other heteroatoms, the resulting reagents effect radical 1,2‐additions to unsaturated substrates, as in the case of selenosulfonation and azidoselenenylation reactions. Other radical processes include oxidations, S H 2 substitutions, single electron transfers, extrusions and fragmentations, and reactions performed on solid supports. The synthetic utility of these processes, as well as mechanistic considerations are covered in this chapter.

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Addition Reactions: Polar Addition

Kočovskí¹

2007

Organic Reaction Mechanisms Series

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Hydroxyselanylation of acyloxycyclohex-3-enes

Cited by 6 publications

References 28 publications

Synthesis of Strophasterols C, E, and F

Synthesis of Strophasterols C, E, and F

Advances in Free Radical Reactions of Organoselenium and Organotellurium Compounds

Addition Reactions: Polar Addition

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