Organocatalytic Asymmetric Domino Knoevenagel/Diels-Alder Reactions: A Bioorganic Approach to the Diastereospecific and Enantioselective Construction of Highly Substituted Spiro[5,5]undecane-1,5,9-triones

A practical and environmentally friendly organocatalytic process for the synthesis of optically active highly substituted spiro[5,5]undecane‐1,5,9‐triones was achieved through the reaction of an aldehyde, an enone, and Meldrum's acid in the presence of a catalytic amount of chiral amino acid (s...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-09, Vol.42 (35), p.4233-4237
Hauptverfasser: Ramachary, D. B., Chowdari, Naidu S., Barbas III, Carlos F.
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Sprache:eng
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Zusammenfassung:A practical and environmentally friendly organocatalytic process for the synthesis of optically active highly substituted spiro[5,5]undecane‐1,5,9‐triones was achieved through the reaction of an aldehyde, an enone, and Meldrum's acid in the presence of a catalytic amount of chiral amino acid (see scheme). The Diels–Alder products were obtained as single diastereomers in excellent yields and enantiomeric excesses.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351916