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Synfacts 2005(0): 0074-0074
DOI: 10.1055/s-2005-869924
DOI: 10.1055/s-2005-869924
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Indium-Mediated Asymmetric Allylation of Aldimines in Methanol
Contributor(s): Paul Knochel, Andrei GavryushinT. Vilayvan*, C. Winotapan, V. Banphavichit, T. Shinada, Y. Ohfune
Chulalongkorn University, Thailand; Osaka City University, Japan
Indium-Mediated Asymmetric Barbier-Type Allylation of Aldimines in Alcoholic Solvents: Synthesis of Optically Active Homoallylic Amines
J. Org. Chem. 2005, 70: 3464-3471
Chulalongkorn University, Thailand; Osaka City University, Japan
Indium-Mediated Asymmetric Barbier-Type Allylation of Aldimines in Alcoholic Solvents: Synthesis of Optically Active Homoallylic Amines
J. Org. Chem. 2005, 70: 3464-3471
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
asymmetric allylation - indium -
Significance
The synthesis of chiral homoallylic amines was easily performed in methanol as a solvent under very mild conditions, thus tolerating a number of functional groups. The reagents and auxiliary used are cheap, and the products can be further transformed into various optically pure products.
Comment
This is probably the simplest route to optically pure homoallylamines from aldehydes. The chiral auxiliary is commercially available and can be removed from the products by a number of ways. Homoallylic amines may serve as intermediates for the synthesis of some important classes of products, therefore such a mild and facile method of their synthesis has been highly desirable.