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Catalytic Asymmetric Diaziridination

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journal contribution
posted on 27.03.2013, 00:00 by Lennart Lykke, Kim Søholm Halskov, Bjørn Dreiø Carlsen, Victor X. Chen, Karl Anker Jørgensen
The first catalytic enantio- and diastereoselective synthesis of diaziridines is presented. Aziridination of N-tosyl aldimines applying modified hydroxylamine under asymmetric phase-transfer catalysis furnished optically active diaziridines. The diaziridines are formed as a single diastereomer in up to 96% ee, containing two orthogonal N-protecting groups, which can be deprotected selectively.