One-Pot Synthesis of Pentasubstituted Cyclohexanes by a Michael Addition Followed by a Tandem Inter-Intra Double Henry Reaction

Michael, Henry, and Henry: A new one‐pot reaction of α,β‐unsaturated aldehydes and β‐dicarbonyls, which involves a Michael reaction catalyzed by diarylprolinol ethers and an inter–intramolecular Henry tandem reaction catalyzed by TBAF (see scheme), has been developed. The reaction proceeds in high e...

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Veröffentlicht in:Chemistry : a European journal 2009-07, Vol.15 (27), p.6576-6580
Hauptverfasser: García Ruano, José Luis, Marcos, Vanesa, Suanzes, Juan Antonio, Marzo, Leyre, Alemán, José
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Sprache:eng
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Zusammenfassung:Michael, Henry, and Henry: A new one‐pot reaction of α,β‐unsaturated aldehydes and β‐dicarbonyls, which involves a Michael reaction catalyzed by diarylprolinol ethers and an inter–intramolecular Henry tandem reaction catalyzed by TBAF (see scheme), has been developed. The reaction proceeds in high enantio‐ and diastereoselectivity for a wide range of unsaturated aldehydes and β‐dicarbonyl reagents. Michael, Henry, and Henry: A new one‐pot reaction of α,β‐unsaturated aldehydes and β‐dicarbonyls, which involves a Michael reaction catalyzed by diarylprolinol ethers and an inter–intramolecular Henry tandem reaction catalyzed by TBAF (see scheme), has been developed. The reaction proceeds in high enantio‐ and diastereoselectivity for a wide range of unsaturated aldehydes and β‐dicarbonyl reagents.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200900894