N-Phosphinyl Phosphoramide — A Chiral Brønsted Acid Motif for the Direct 
Asymmetric N,O-Acetalization of Aldehydes

Vellalath, Sreekumar; Čorić, Ilija; List, Benjamin

doi:10.1002/anie.201005347

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N-Phosphinyl Phosphoramide — A Chiral Brønsted Acid Motif for the Direct Asymmetric N,O-Acetalization of Aldehydes

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Vellalath, Sreekumar
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Čorić, Ilija
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Vellalath, S., Čorić, I., & List, B. (2010). N-Phosphinyl Phosphoramide — A Chiral Brønsted Acid Motif for the Direct Asymmetric N,O-Acetalization of Aldehydes. Angewandte Chemie International Edition, 49(50), 9749-9752. doi:10.1002/anie.201005347.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-8D9B-6

Abstract

Fine‐tuning the sites: The readily accessible N‐phosphinyl phosphoramide 1 proved to be highly efficient and enantioselective in catalyzing the title reaction. The synthetic utility of this methodology was demonstrated with the first catalytic asymmetric synthesis of the analgesic pharmaceutical (R)‐chlorothenoxazine (see scheme).