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Synfacts 2007(1): 0018-0018
DOI: 10.1055/s-2006-955754
DOI: 10.1055/s-2006-955754
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Hydroamination Route to Hexahydroindoles
R. Lebeuf, F. Robert, K. Schenk, Y. Landais*
UniversitÉ Bordeaux-1, Talence, France and UniversitÉ de Lausanne, Switzerland
Further Information
Publication History
Publication Date:
15 December 2006 (online)
Significance
A formal intramolecular hydroamination of cyclohexa-2,5-dienes to the corresponding bicyclic allylic amines with high diastereoselectivity is reported. A mechanism involving a deprotonation with a subsequent stereoselective intramolecular protonation followed by addition of the resulting lithium amide to the 1,3-diene is proposed. The structure of one of the bicyclic allylic amine products was determined by an X-ray crystallographic analysis.