10.1021/ja045608c.s001
Joseph M. Mahoney
Joseph M.
Mahoney
Colin R. Smith
Colin R.
Smith
Jeffrey N. Johnston
Jeffrey N.
Johnston
Brønsted Acid-Promoted Olefin Aziridination and Formal
<i>a</i><i>nti</i>-Aminohydroxylation
American Chemical Society
2005
Active ester substrates
protonated aziridine
triflic acid
azide
nucleophilic carbonyl
triazoline need
olefin aminohydroxylation
aziridine production
N 2
2005-02-09 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Br_nsted_Acid_Promoted_Olefin_Aziridination_and_Formal_i_a_i_i_nti_i_Aminohydroxylation/3301735
A straightforward synthesis of aziridines is reported from an electron-rich azide (alkyl or aryl azide), electron-deficient olefin, and triflic acid in cold acetonitrile. The only coproduct of the reaction is dinitrogen (N<sub>2</sub>). Active ester substrates bearing a nucleophilic carbonyl engage the putative protonated aziridine intermediate to produce the product of olefin aminohydroxylation in which the nitrogen is benzyl protected and the oxygen is acylated. The possibility that a triazoline need not be an intermediate in aziridine production is advanced.