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

Authors :
Tiddens, Martine R
Klein Gebbink, Robertus J M
Otte, Matthias
Organic Chemistry and Catalysis
Sub Organic Chemistry and Catalysis
Source :
Organic Letters, 18(15), 3714. American Chemical Society : Division of Carbohydrate Chemistry
Publication Year :
2016
Publisher :
American Chemical Society (ACS), 2016.

Abstract

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.

Details

ISSN :
15237052 and 15237060
Volume :
18
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....26e647efbae1687b49fe7dc9980eca53