doi: 10.1021/jo0477244.
Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: synthesis of optically active homoallylic amines
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- PMID: 15844979
- DOI: 10.1021/jo0477244
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Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: synthesis of optically active homoallylic amines
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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