The B(C6F5)3‑Catalyzed Tandem Meinwald Rearrangement–Reductive Amination

A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B­(C6F5)3 resulting in the first tandem Meinwald rearrangement–reducti...

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Veröffentlicht in:Organic letters 2016-08, Vol.18 (15), p.3714-3717
Hauptverfasser: Tiddens, Martine R, Klein Gebbink, Robertus J. M, Otte, Matthias
Format: Artikel
Sprache:eng
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Zusammenfassung:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B­(C6F5)3 resulting in the first tandem Meinwald rearrangement–reductive amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01744