Utilizing the Asymmetric Amino-Cope Rearrangement as a Novel Approach to Enantiomerically Enriched 3-Substituted Aldehydes

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

ACKNOWLEDGMENTS

We thank Syngenta (joint studentship support to C. H. P.), GlaxoSmithKline (joint studentship to M. E.), and the University of Loughborough for facilities and financial support.