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  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, 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.

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 Creators:
Blaser, E1, Author
Kolar, P1, Author
Fenske, D1, Author
Goesmann, H1, Author
Waldmann, Herbert2, Author           
Affiliations:
1external, ou_persistent22              
2Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753290              

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Free keywords: ORGANIC-SYNTHESIS; N-GLYOXYLOYL-(2R)-BORNANE-10,2-SULTAM; ALDEHYDES; CATALYSIS; CHEMISTRY Chemistry; asymmetric synthesis; chiral auxiliaries; cycloadditions; lanthanides; delta-lactones;
 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.

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Language(s): eng - English
 Dates: 1999-01
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000077978100045
 Degree: -

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Title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Source Genre: Journal
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Publ. Info: Weinheim : WILEY-VCH
Pages: - Volume / Issue: (1) Sequence Number: - Start / End Page: 329 - 333 Identifier: ISSN: 1434-193X