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2005
Aziridine derivatives
R 0040
Rhodium(II)-Catalyzed Aziridination of Allyl-Substituted Sulfonamides and Carbamates. — Treatment of unsaturated sulfonamides with PhI(OAc)2, MgO, and cata03- 108 lytic
amounts of Rh2(OAc)4 affords aziridinothiazol and -thiazine derivatives in excellent yields. These products undergo regioselective ring opening of the aziridine ring to
provide ring-expanded products (VIII). In contrast, the aziridination reaction of cycloalkenyl carbamates does not require a Rh(II) catalyst. The resulting tricyclic aziridine products give by treatment with nucleophiles anti-derived spiro products. Indolyland benzofuranyl carbamates require a rhodium catalyst for the cyclization reaction,
which leads in the presence of nucleophiles to spiro products, predominantly as syn-isomers for indolyl carbamates and with low stereoselectivity for the benzofuran carbamate. — (PADWA*, A.; FLICK, A. C.; LEVERETT, C. A.; STENGEL, T.; J. Org.
Chem. 69 (2004) 19, 6377-6386; Dep. Chem., Emory Univ., Atlanta, GA 30322, USA;
Eng.) — Klein
2005
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