Indium-Mediated Asymmetric Barbier-Type Allylation of Aldimines in Alcoholic Solvents:  Synthesis of Optically Active Homoallylic Amines

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 p...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-04, Vol.70 (9), p.3464-3471
Main Authors: Vilaivan, Tirayut, Winotapan, Chutima, Banphavichit, Vorawit, Shinada, Tetsuro, Ohfune, Yasufumi
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0477244