Indium-catalyzed Barbier reactions of amino aldehydes

Authors
Steurer, S Podlech, J
Citation
S. Steurer et J. Podlech, Indium-catalyzed Barbier reactions of amino aldehydes, ADV SYNTH C, 343(3), 2001, pp. 251-254
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ADVANCED SYNTHESIS & CATALYSIS
ISSN journal
16154150 → ACNP
Volume
343
Issue
3
Year of publication
2001
Pages
251 - 254
Database
ISI
SICI code
1615-4150(200104)343:3<251:IBROAA>2.0.ZU;2-K
Abstract
The indium-catalyzed Barbier-type reaction of Cbz-protected amino aldehydes with methyl 2-(bromomethyl)acrylate in the presence of aluminum or mangane se/Me3SiCl was investigated. Best results were obtained using 0.15 equiv. I nCl3 with excess aluminum. No significant differences between catalyzed and stoichiometric reaction conditions were observed. Addition of chiral auxil iaries did not improve selectivities in indium-mediated allyl additions.