Gold catalysis: one-pot alkylideneoxazoline synthesis/alder-ene reaction
Based on the gold-catalyzed synthesis of methyleneoxazolines, a one-pot combination with an Alder-ene reaction was developed. For azodicarboxylates, good to very good yields (51-99 %) of the oxazolemethylhydrazinedicarboxylates were achieved with 3 mol % of the Gagosz catalyst, [Ph3PAuNTf3]. In a le...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
20 March 2012
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| In: |
Chemistry
Year: 2012, Volume: 7, Issue: 6, Pages: 1435-1442 |
| ISSN: | 1861-471X |
| DOI: | 10.1002/asia.201200046 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/asia.201200046 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/asia.201200046 
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| Author Notes: | A. Stephen K. Hashmi and Anna Littmann |
| Summary: | Based on the gold-catalyzed synthesis of methyleneoxazolines, a one-pot combination with an Alder-ene reaction was developed. For azodicarboxylates, good to very good yields (51-99 %) of the oxazolemethylhydrazinedicarboxylates were achieved with 3 mol % of the Gagosz catalyst, [Ph3PAuNTf3]. In a less-selective reaction, 4-phenyl-3H-1,2,4-triazol-3,5(4 H)-dione gave lower yields (41-49 %) of the corresponding oxazolemethylphenyltriazolidinediones. Overall, five new bonds were formed. Tetracyanoethylene afforded a cyclobutane derivative through a [2+2] cycloaddition reaction at −40 °C, but only 45 % of the spiro compound was obtained. The less-readily available KITPHOS ligands on gold gave even higher yields at lower catalyst loadings (2 mol %), but longer reaction times were required. |
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| Item Description: | Gesehen am 06.09.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1861-471X |
| DOI: | 10.1002/asia.201200046 |