Sequential Au/Cu catalysis

• Verfasst von: Nalivela, Kumara Swamy [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Sequential Au/Cu catalysis
• Titelzusatz: a two catalyst one-pot protocol for the enantioselective synthesis of oxazole α-hydroxy esters via intramolecular cyclization/intermolecular Alder-ene Reaction
• Verf.angabe: Kumara Swamy Nalivela, Matthias Rudolph, Elham S. Baeissa, Basma G. Alhogbi, Ibraheem A.I. Mkhalid, A. Stephen K. Hashmi
• E-Jahr: 2018
• Jahr: 06 April 2018
• Umfang: 8 S.
• Fussnoten: Gesehen am 29.08.2018
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Ort Quelle: Weinheim : Wiley-VCH, 2001
• Jahr Quelle: 2018
• Band/Heft Quelle: 360(2018), 11, Seite 2183-2190
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201800246
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: gold catalysis
• Sach-SW: alkylglyoxylate
• Sach-SW: heterocycles
• Sach-SW: oxazole α-hydroxy ester
• Sach-SW: Propargylamides
• K10plus-PPN: 1580483887

Abstract

A convenient protocol for the enantioselective synthesis of oxazole α-hydroxy ester derivatives 4 from readily available propargylamides 1 and alkylglyoxylates 3 was developed. The first step of the one-pot procedure is the selective intramolecular in situ formation of an alkylideneoxazoline 2, which then in an intermolecular reaction is enantioselectively transformed to the oxazole α-hydroxy ester derivatives 4 in quantitative yield and good to excellent enantioselectivity via an asymmetric copper(II)-catalyzed Alder-ene reaction.