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Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines
| Content Provider | Semantic Scholar |
|---|---|
| Author | Kerr, Ryan W. F. Greenhalgh, Mark D. Slawin, Alexandra M. Z. Arnold, Polly L. Smith, Andrew D. |
| Copyright Year | 2017 |
| Abstract | Abstract An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations. |
| Starting Page | 125 |
| Ending Page | 134 |
| Page Count | 10 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/j.tetasy.2016.10.012 |
| Volume Number | 28 |
| Alternate Webpage(s) | https://research-repository.st-andrews.ac.uk/bitstream/handle/10023/10090/Kerr_2017_Enantioselective_Tetrahedron_CC.pdf?isAllowed=y&sequence=1 |
| Alternate Webpage(s) | https://doi.org/10.1016/j.tetasy.2016.10.012 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
