Publikation:

3-Substituted and 2,3-Disubstituted Cyclopentanones via an Asymmetric Tandem 1,4-Addition/Dieckmann Cyclization

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3_Substituted.pdf
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Datum

2004

Autor:innen

Halfbrodt, Wolfgang
Kalogerakis, Aris
Köhler, Thomas
Kreye, Paul

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URI (zitierfähiger Link)
http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-46272
DOI (zitierfähiger Link)
https://doi.org/10.1055/s-2003-45008
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Attribution-NonCommercial-NoDerivs 2.0 Generic

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Open Access-Veröffentlichung
Open Access Green

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Chemie: Publikationen
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Published

Erschienen in

Synlett. 2004(2), pp. 291-294. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2003-45008

Zusammenfassung

A new stereoselective method for the synthesis of 3-substituted and 2,3-disubstituted cyclopentanones is described. The key step is the 1,4-addition of a cuprate to a chilar Michael-acceptor derived from (-)-8-phenylmenthol or the Helmchen auxiliary followed by Dieckmann cyclization of the obtained chiral enolates. The resultant 2,3-cyclopentanones can be transformed after methanolysis and demethoxycarbonylation to the related 3-substituted ­cyclopentanones.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

asymmetric synthesis, cyclopentanones, cuprate, chiral auxiliary, 1,4-addition, Dieckmann cyclization, natural products

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ISO 690GROTH, Ulrich, Wolfgang HALFBRODT, Aris KALOGERAKIS, Thomas KÖHLER, Paul KREYE, 2004. 3-Substituted and 2,3-Disubstituted Cyclopentanones via an Asymmetric Tandem 1,4-Addition/Dieckmann Cyclization. In: Synlett. 2004(2), pp. 291-294. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2003-45008
BibTex
@article{Groth20043Subs-10048,
  year={2004},
  doi={10.1055/s-2003-45008},
  title={3-Substituted and 2,3-Disubstituted Cyclopentanones via an Asymmetric Tandem 1,4-Addition/Dieckmann Cyclization},
  number={2},
  issn={0936-5214},
  journal={Synlett},
  pages={291--294},
  author={Groth, Ulrich and Halfbrodt, Wolfgang and Kalogerakis, Aris and Köhler, Thomas and Kreye, Paul}
}
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