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

作者：Allin Steven M^*; Horro Pita Catarina; Essat Munira; Aspinall Ian; Shah Pritom

来源：Synthetic Communications, 2010, 40(18): 2696-2711.

DOI：10.1080/00397910903318666

• Aldehyde
• aminoalcohol
• amino-Cope
• asymmetric
• rearrangement

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.

• 出版日期2010