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Synfacts 2005(0): 0074-0074  
DOI: 10.1055/s-2005-869924
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Indium-Mediated Asymmetric Allylation of Aldimines in Methanol

Rezensent(en): Paul Knochel, Andrei Gavryushin
T. 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  
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Publikationsdatum:
20. Juli 2005 (online)

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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.

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