216306-33-1Relevant academic research and scientific papers
Utilizing the asymmetric amino-cope rearrangement as a novel approach to enantiomerically enriched 3-substituted aldehydes
Allin, Steven M.,Horro-Pita, Catarina,Essat, Munira,Aspinall, Ian,Shah, Pritom
experimental part, p. 2696 - 2711 (2010/11/02)
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.
High asymmetric induction in anionic amino-cope rearrangements controlled by β-aminoalcohol auxiliaries
Allin, Steven M.,Button, Martin A. C.,Baird, Robert D.
, p. 1117 - 1119 (2007/10/03)
Novel 3-amino-1,5-dienes were prepared with high diastereoselectivity by unprecedented 1,2-addition of allyl Grignard to α,β-unsaturated imines containing β-aminoalcohol auxiliaries. Asymmetric anionic amino-Cope rearrangement of the diastereoisomerically pure 3-amino-1,5-diene substrates proceeded to yield the target 3-substituted aldehyde in good yield and with high levels of asymmetric induction (up to 94% e.e.).
