Alkenes From three-membered heterocycles

By Wittig and related reactions (3-Dimethylaminopropyl)-triphenylphosphorane, 119 Sodium amide, 278 Vinyl(triphenyl)phosphonium bromide, 343 (E)-Alkenes By elimination reactions Arylselenocarboxamides, 22 Dichlorobis(cyclopentadienyl)-titanium, 102 Hydrogen peroxide, 145 From three-membered heterocycles Tributyltinlithium-Trimethylalu-minum, 320 Trisubstituted alkenes Chloromethyldiphenylsilane, 74 Organocopper reagents, 207 Alkenes (Methods to form alkenes)... 

In addition to epoxides, three-membered nitrogen heterocycles, aziridines, can be obtained by means of catalytic asymmetric aziridinations (Eq. 30). To this aim, chiral ruthenium(salen) complexes 67 [56] and 68 [57] were useful (Fig. 1). The former phosphine complexes 67 gave the aziridine from two cy-cloalkenes with 19-83% ee [56]. On the other hand, terminal alkenes selectively underwent aziridination in the presence of the latter carbonyl complex 68 with 87-95% ee [57]. In these examples, N-tosyliminophenyliodinane or N-tosyl azide were used as nitrene sources. Quite recently, catalytic intramolecular ami-dation of saturated C-H bonds was achieved by the use of a ruthenium(por-phyrin) complex (Eq. 31) [58]. In the presence of the ruthenium catalyst and 2 equiv iodosobenzene diacetate, sulfamate esters 69 were converted into cyclic sulfamidates 70 in moderate-to-good yields. 

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