High Asymmetric Induction in Anionic Amino-Cope Rearrangements Controlled by β-Aminoalcohol Auxiliaries

Steven M. Allin; Martin A. C. Button; Robert D. Baird

doi:10.1055/s-1998-1880

Synlett 1998; 1998(10): 1117-1119
DOI: 10.1055/s-1998-1880

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High Asymmetric Induction in Anionic Amino-Cope Rearrangements Controlled by β-Aminoalcohol Auxiliaries

Steven M. Allin^* , Martin A. C. Button, Robert D. Baird

^*Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, England; Fax 44(0)15 09 22 39 25; E-mail: S.M.Allin@lboro.ac.uk

Abstract

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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.).

α,β-unsaturated imine - β-aminoalcohol - amino-Cope - sigmatropic rearrangement - asymmetric induction

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