Radical denitradon

Seqnendal Michael addidons are versatile methods for the constnicdon of cyclic compounds. Although a variety of these reacdons have been developed, the use of alcohols as nucleophiles for the Michael addidon to nltroalkenes has been little studied. Recently, Dteda and coworkers have reported an elegant synthesis of octahydtobett2o[li furans via the seqnendal Michael addidon of 1-nltro-cyclohexenev/ith methyl4-hydroxy-2-bittynoatein the presence of r-BnOK followed by radical denitradon fEq. 7.74. ... 

The Diels-Alder reacdon followed by radical denitradon provides a nseftd strategy for constnicdon of six-membered compounds, in which thenitro group accelerates the reacdon and also controls the reglo-chemistry of the addidon fEq. 7.75. ... 

Thus, radical denitradon has developed as a reliable tool in organic synthesis and has been mainly carried out using dn hydnde in total syntheses of natural products. There is one report in which NaTeH was used for removing the nitro group. Norslanadione, a biologically acdve... 

The difficulty in controlling the regiochemistry during radical-denitradon of allylic nitre compounds is well known The migradon of the double bond is a serious problem, as shown in Eq 7 96 This problem is overcome by ahydnde transfer reacdon in the presence of a palladiuir catalyst fEq 7 97 ... 

The regiochemical control of Pd-catalyzed hydnde transfer reacdon is much more effeedve than that of the radical denitradon, as Shown in Eq 7 98 The base-catalyzed reacdon of nitroolefins with aldehydes followed by denitradon provides a new syntbedc method of homoallyl aicohols fEq 7 99 Exomethylene compounds are obtined by denitradon of cyclic allylic nino compounds with PdfO, HGO-,H and Et- N fEq 7 100 ... 

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