Gold catalysis: 1,3-oxazines by cyclisation of allene amides
A series of allene amides was prepared and their gold-catalysed cyclisation was investigated. The formation of six-membered rings, 1,3-oxazines, was observed. Dihydropyrroles originating from intramolecular hydroamination of the distal CC double bonds of the allenes were minor side products. Mechan...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
12 April 2011
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| In: |
Chemistry - a European journal
Year: 2011, Volume: 17, Issue: 20, Pages: 5661-5667 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201100132 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201100132 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201100132 
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| Author Notes: | A. Stephen K. Hashmi, Andreas M. Schuster, Sebastian Litters, Frank Rominger, and Markus Pernpointner |
| Summary: | A series of allene amides was prepared and their gold-catalysed cyclisation was investigated. The formation of six-membered rings, 1,3-oxazines, was observed. Dihydropyrroles originating from intramolecular hydroamination of the distal CC double bonds of the allenes were minor side products. Mechanistic studies by in situ 31P NMR spectroscopy showed only one additional species during the conversion in each case; a computational study of the different allyl gold(I) species involved allowed this to be assigned as the σ-allyl gold species bearing the gold catalyst at the sterically less hindered methylene end. The regiospecific deuterodeauration of this intermediate confirmed a SE′-type mechanism for this last step of the catalytic cycle. |
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| Item Description: | Gesehen am 07.09.2022 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201100132 |