Ring Closing Metathesis for the Asymmetric Synthesis of (S)-Homopipecolic Acid, (S)-Homoproline and (S)-Coniine

Stephen G. Davies; Keiji Iwamoto; Christian A. P. Smethurst; Andrew D. Smith; Humberto Rodriguez-Solla

doi:10.1055/s-2002-32580

LETTER

Ring Closing Metathesis for the Asymmetric Synthesis of (S)-Homopipecolic Acid, (S)-Homoproline and (S)-Coniine

Stephen G. Davies*, Keiji Iwamoto, Christian A. P. Smethurst, Andrew D. Smith, Humberto Rodriguez-Solla
The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
e-Mail: steve.davies@chem.ox.ac.uk;

Abstract

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Abstract

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

Key words

lithium amide - conjugate addition - ring closing metathesis - asymmetric synthesis - cyclic β-amino acids

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Referenzen

References

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