Beilstein J. Org. Chem.2011,7, 824–830, doi:10.3762/bjoc.7.94
chloride provides functionalized homoallylic amines. An intramolecular version of this process leads to 3-aminotetrahydrofurans and 3-aminotetrahydropyrans.
Keywords: allene; 3-aminotetrahydrofurans; 3- and 4-aminotetrahydropyrans; hydrozirconation; nitrile; transmetalation; Introduction
The reversible
to depend on the allene substitution. The intramolecular variant of this reaction was used to prepare 3-aminotetrahydrofurans and 3-aminotetrahydropyrans, and these addition products can subsequently be transformed into synthetically valuable β-amino acid building blocks.
Coupling constant analysis
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Graphical Abstract
Scheme 1:
One-pot hydrozirconation-reductive coupling of allene 2 and nitrile 7.