Malkov, A.V., Barłóg, M., Miller-Potucká, L., Kabeshov, M.A., Farrugia, L.J. and Kočovský, P. (2012) Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: a convenient synthesis of Di- and tri-substituted isoxazolidines and β-Amino-δ-hydroxy esters. Chemistry: A European Journal, 18(22), pp. 6873-6884. (doi: 10.1002/chem.201102716)
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Publisher's URL: http://dx.doi.org/10.1002/chem.201102716
Abstract
Enantiopure, Boc-protected alkoxyamines 12 and 13, derived from the readily available homoallylic alcohols 4 via a reaction that involves either inversion or retention of configuration, undergo a diastereoselective Pd-catalyzed ring-closing carbonylative amidation to produce isoxazolidines 16/17 (≤50:1 diastereoisomer ratio (d.r.)) that can be readily converted into the N-Boc-protected esters of β-amino-δ-hydroxy acids and their γ-substituted homologues 37. The key carbonylative cyclization proceeds through an unusual syn addition of the palladium and the nitrogen nucleophile across the C[DOUBLE BOND]C bond (19→21), as revealed by the reaction of 15, which afforded isoxazolidine 18 with high diastereoselectivity.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Malkov, Dr Andrei and Farrugia, Dr Louis and Kabeshov, Mr Mikhail |
| Authors: | Malkov, A.V., Barłóg, M., Miller-Potucká, L., Kabeshov, M.A., Farrugia, L.J., and Kočovský, P. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Chemistry: A European Journal |
| Journal Abbr.: | Chem. Eur J. |
| ISSN: | 0947-6539 |
| ISSN (Online): | 1521-3765 |
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