Oxidative ring-opening of aziridine-1-carboxylates with sulphoxides
1970; Elsevier BV; Volume: 26; Issue: 18 Linguagem: Inglês
10.1016/s0040-4020(01)93080-7
ISSN1464-5416
AutoresS. FUJITA, Tamejiro Hiyama, H. NOZAKI,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoThe title reaction furnishes a practical preparation of α-carbalkoxyamino ketones from nitrene adducts of the corresponding olefins. The aziridines are alternatively accessible via addition ,of iodine isocyanate, alcoholysis and elimination of hydrogen iodide. DMSO-cleavage of cis and trans isomers of 1-carbethoxy-2-methyl-3-phenylaziridine proceeds regioselectively: the cis isomer reacts at 1,2-bond and 1,3-bond in a ratio of ca 1:1, whereas the trans isomer reacts at 1,3-bond almost exclusively. The 1,3-bond cleavage is predominant under acidic conditions for both isomers. Under neutral conditions, the cleavage proceeds via an SN2 type transition state.
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