Arylic and alkylic imines, activated with BF3.OEt2 react with different allylic bromides in the presence of CrCl2 to give the corresponding homo allylic amines. The reaction can be performed in a single step starting from the aldehyde and the amine, in the presence of molecular sieves (4 angstrom), in a sort of amino-allylation of aldehydes. With the imine derived from benzaldehyde and (S)-valine a good diastereomeric excess (86%) is obtained.
Giammaruco, M., Taddei, M., Ulivi, P. (1993). A Modification of the Hiyama Reaction - Synthesis of Homo Allylic Amines From Imines and Allylic Bromides In the Presence of Crcl2. TETRAHEDRON LETTERS, 34(22), 3635-3638 [10.1016/S0040-4039(00)73656-2].
A Modification of the Hiyama Reaction - Synthesis of Homo Allylic Amines From Imines and Allylic Bromides In the Presence of Crcl2
Taddei, Maurizio;
1993-01-01
Abstract
Arylic and alkylic imines, activated with BF3.OEt2 react with different allylic bromides in the presence of CrCl2 to give the corresponding homo allylic amines. The reaction can be performed in a single step starting from the aldehyde and the amine, in the presence of molecular sieves (4 angstrom), in a sort of amino-allylation of aldehydes. With the imine derived from benzaldehyde and (S)-valine a good diastereomeric excess (86%) is obtained.
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https://hdl.handle.net/11365/31040
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