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

Martine R Tiddens; Robertus J M Klein Gebbink; Matthias Otte

doi:10.1021/acs.orglett.6b01744

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

Martine R Tiddens, Robertus J M Klein Gebbink, Matthias Otte^*

^*Corresponding author for this work

Sub Organic Chemistry and Catalysis

Research output: Contribution to journal › Article › Academic › peer-review

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.

Original language	English
Pages (from-to)	3714-3717
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.6b01744
Publication status	Published - 5 Aug 2016

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title = "The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination",

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.",

author = "Tiddens, {Martine R} and {Klein Gebbink}, {Robertus J M} and Matthias Otte",

year = "2016",

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T1 - The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination

AU - Tiddens, Martine R

AU - Klein Gebbink, Robertus J M

AU - Otte, Matthias

PY - 2016/8/5

Y1 - 2016/8/5

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.6b01744

DO - 10.1021/acs.orglett.6b01744

M3 - Article

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SN - 1523-7060

VL - 18

SP - 3714

EP - 3717

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

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

Abstract

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