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2005
Ring closure reactions
O 0130
Broensted Acid-Promoted Olefin Aziridination and Formal anti-Aminohy— The addition of electron-rich azides towards electron-deficient olefins
24- 047 droxylation.
is efficiently catalyzed by Broensted acids like triflic acid and provides aziridines (III)
in good yields. In a similar manner, triflic acid-catalyzed aminohydroxylation of
carbamates (IV) and (VI) with azide (IIa) gives oxazoles (V) and (VII) in good yields
and diastereoselectivities. This reaction is stereocomplementary to traditional metal-mediated aminohydroxylations that provide syn-amino alcohols from E-olefins. —
(MAHONEY, J. M.; SMITH, C. R.; JOHNSTON*, J. N.; J. Am. Chem. Soc. 127
(2005) 5, 1354-1355; Dep. Chem., Indiana Univ., Bloomington, IN 47405, USA;
Eng.) — Mischke
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