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. 2005 Apr 29;70(9):3464-71.
doi: 10.1021/jo0477244.

Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: synthesis of optically active homoallylic amines

Tirayut Vilaivan  1 , Chutima Winotapan, Vorawit Banphavichit, Tetsuro Shinada, Yasufumi Ohfune
Affiliations

Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: synthesis of optically active homoallylic amines

Tirayut Vilaivan et al. J Org Chem. .

Abstract

[reaction: see text] Chiral aldimines derived from phenylglycinol were diastereoselectively allylated with indium powder/allyl bromide in alcoholic solvents. Both aliphatic and aromatic aldimines provided good yield of the desired products with high diastereoselectivity. A racemization-free protocol for removal of the phenylglycinol auxiliary was also developed. The stereochemical assignment of the homoallylic amine was made by NMR spectroscopy and a transition state model was proposed to explain the selectivity.

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