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. 2011:7:824-30.
doi: 10.3762/bjoc.7.94. Epub 2011 Jun 17.

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles

Peter Wipf  1 , Marija D Manojlovic
Affiliations

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles

Peter Wipf et al. Beilstein J Org Chem. 2011.

Abstract

The one-pot hydrozirconation of allenes and nitriles followed by an in situ transmetalation of the allylzirconocene with dimethylzinc or zinc chloride provides functionalized homoallylic amines. An intramolecular version of this process leads to 3-aminotetrahydrofurans and 3-aminotetrahydropyrans.

Keywords: 3- and 4-aminotetrahydropyrans; 3-aminotetrahydrofurans; allene; hydrozirconation; nitrile; transmetalation.

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Figures

Scheme 1
Scheme 1
One-pot hydrozirconation-reductive coupling of allene 2 and nitrile 7.
Scheme 2
Scheme 2
Cyclization of allenylnitrile 18.
Figure 1
Figure 1
Coupling constant analysis of the Boc-protected aminopyran ring in 21.
Scheme 3
Scheme 3
Proposed chelated transition state model.
Scheme 4
Scheme 4
Conversion of homoallylic amines to β-amino acid derivatives.
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