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Allylic aryl-selenoxides

DFT has been used to model the endo and exo transition states for [2,3]-sigmatropic rearrangement of allylic aryl-selenoxides and -selenimides. °... [Pg.484]

Enantioselective oxidation of Z-aryl cinnamyl allylic selenide (83) with oxaziridine (—)-(69) gave 1-phenyl allyl alcohol (85) via an allyl selenoxide-selenate [2,3] sigmatropic rearrangement (Scheme... [Pg.387]

En route to a total synthesis of the anticancer compound FR901464, Koide and coworkers carried out a diastereoselective allylic selenoxide rearrangement upon oxidation of either allyl selenide 251 [Scheme 18.641. Optimization studies using the preformed allyl selenide 251 identified the o-nitrophenyl selenide as an effective aryl substituent and N,N-dimethylaminopyridine as the best selenophilic base additive in the formation of rearrangement product 252 (see top of Scheme 18.641. Reactions were slower and diastereoselectivity, a crucial parameter here, was lower using other bases or with less than 3 equiv of DMAP. Using the optimized conditions, a one-pot method for overall 1,3-allylic alcohol transposition was... [Pg.736]

See other pages where Allylic aryl-selenoxides is mentioned: [Pg.54]    [Pg.168]    [Pg.340]    [Pg.36]    [Pg.484]    [Pg.772]    [Pg.772]    [Pg.48]    [Pg.205]    [Pg.215]    [Pg.217]    [Pg.157]    [Pg.605]    [Pg.17]    [Pg.48]    [Pg.205]    [Pg.215]    [Pg.217]    [Pg.772]   
See also in sourсe #XX -- [ Pg.484 ]



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