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Utilizing the Asymmetric Amino-Cope Rearrangement as a Novel Approach to Enantiomerically Enriched 3-Substituted Aldehydes |
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| Authors: | Steven M. Allin Catarina Horro-Pita Munira Essat Ian Aspinall Pritom Shah |
| Affiliation: | 1. School of Chemical and Geographical Sciences, Keele University , Keele, United Kingdom s.m.allin@chem.keele.ac.uk;3. Department of Chemistry , Loughborough University , Loughborough, United Kingdom;4. Syngenta, Jealott's Hill Research Centre , Bracknell, United Kingdom;5. GlaxoSmithKline , Stevenage, United Kingdom |
| Abstract: | We report the asymmetric amino-Cope rearrangement of some novel 3-amino-1,5-diene substrates to yield enantiomerically enriched 3-alkyl and 3-aryl aldehyde products. We have developed a system that gives excellent and comparable levels of product enantiomeric excess (ee) for both alkyl- and aryl-substituted products. Our results have implications for the control of the mechanistic pathway of the amino-Cope rearrangement and thus its potential utility in asymmetric synthesis. |
| Keywords: | Aldehyde aminoalcohol amino-Cope asymmetric rearrangement |