Asymmetric steering of oxa Diels-Alder reactions with silyloxydienes employing 
proline esters as chiral auxiliary groups

Blaser, E; Kolar, P; Fenske, D; Goesmann, H; Waldmann, Herbert

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Asymmetric steering of oxa Diels-Alder reactions with silyloxydienes employing proline esters as chiral auxiliary groups

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Waldmann, Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Blaser, E., Kolar, P., Fenske, D., Goesmann, H., & Waldmann, H. (1999). Asymmetric steering of oxa Diels-Alder reactions with silyloxydienes employing proline esters as chiral auxiliary groups. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (1), 329-333.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-7132-C

Abstract

Chiral aldehydes 4a,b, obtained by the ozonolysis of the corresponding N,N'-fumaroylbis[(S)-proline esters] 3 react in the presence of lanthanoid chelate complexes Eu(fod)(3) or Eu(hfc)(3) with silyloxydienes 7 or 12 to give delta-lactones 10 or dihydro-gamma-pyrones 13 with very high diastereomeric ratios (up to 99:1). The absolute configuration of the predominating diastereoisomer of compound 10b was unequivocally determined by X-ray structural analysis.