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Direct Synthesis of Unprotected 2-Azidoamines from Alkenes via an Iron-Catalyzed Difunctionalization Reaction

preprint
submitted on 02.04.2020 and posted on 03.04.2020 by Szabolcs Makai, Eric Falk, Bill Morandi

Unprotected, primary 2-azidoamines are versatile precursors to vicinal diamines, which are among the most common motifs in biologically active compounds. Herein, we report their operationally simple synthesis through an iron-catalyzed difunctionalization of alkenes. A wide array of alkene substrates are tolerated, including complex drug-like molecules and a tripeptide. Facile derivatizations of the azidoamine group demonstrate the versatility of this masked diamine motif in chemoselective, orthogonal transformations. Applications of the methodology in the concise synthesis of RO 20-1724 and in a formal total synthesis of (±)-hamacanthin B further demonstrate the broad synthetic potential of this highly functional group tolerant reaction.

Funding

Swiss National Science Foundation (SNSF 184658)

ETH Zürich

History

Email Address of Submitting Author

morandib@ethz.ch

Institution

ETH Zurich

Country

Switzerland

ORCID For Submitting Author

0000-0003-3968-1424

Declaration of Conflict of Interest

no COI

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