Publikation: 3-Substituted and 2,3-Disubstituted Cyclopentanones via an Asymmetric Tandem 1,4-Addition/Dieckmann Cyclization
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2004
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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
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asymmetric synthesis, cyclopentanones, cuprate, chiral auxiliary, 1,4-addition, Dieckmann cyclization, natural products
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GROTH, 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-2003-45008BibTex
@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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