Microwave assisted hydroaminomethylation of alkenes

Hydroaminomethylation of terminal alkenes can be regioselectively carried out in less than 30 min with secondary amines in EtOH under MW irradiation using (PPh 3) 3RhCO(H) and Xantphos or Biphephos as ligands. When primary amines were employed, the corresponding enamines were obtained in good yields...

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Bibliographic Details
Published in:Tetrahedron letters 2007-11, Vol.48 (48), p.8501-8504
Main Authors: Petricci, Elena, Mann, André, Salvadori, Jessica, Taddei, Maurizio
Format: Article
Language:English
Subjects:
Amine
Amino acids
Deprotection
Hydroformylation
Microwaves
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Summary:Hydroaminomethylation of terminal alkenes can be regioselectively carried out in less than 30 min with secondary amines in EtOH under MW irradiation using (PPh 3) 3RhCO(H) and Xantphos or Biphephos as ligands. When primary amines were employed, the corresponding enamines were obtained in good yields. Tris-benzyl allylglycine was transformed into different (basic) benzylated α-amino acids. Moreover, the benzyl protection was removed in few minutes under MW irradiation with Pd(OH) 2 under H 2 atmosphere.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.09.154