The first organocatalytic hetero-domino Knoevenagel-Diels-Alder-epimerization reactions: Diastereoselective synthesis of highly substituted spiro[cyclohexane-1,2 '-indan]-1 ',3 ',4-triones

L-Proline and pyrrolidine catalyzed the three component hetero-domino Knoevenagel-Diels-Alder-Epimerization reactions of readily available precursors enones 1a-i, arylaldehydes 2a-i and 1,3-indandione 3 to furnish highly substituted prochiral spiro[cyclohexane- 1,2'-indan]-1',3',4-tri...

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Bibliographic Details
Published inSynlett no. 12; pp. 1910 - 1914
Main Authors Ramachary, DB, Chowdari, NS, Barbas, CF
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 29.09.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MELDRUMS ACID
ORGANIC-SYNTHESIS
BENZOANNELATED CENTROPOLYQUINANES
ALPHA-AMINO
ALPHA,BETA-UNSATURATED KETONES
ONE-POT SYNTHESIS
organic Lewis acid
2-amino-1,3-butadiene
ASSEMBLY REACTIONS
organocatalysis
domino reactions
ASYMMETRIC ALDOL REACTIONS
Diels-Alder reaction
MICHAEL ADDITIONS
AMINO-ACID-DERIVATIVES
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Summary:L-Proline and pyrrolidine catalyzed the three component hetero-domino Knoevenagel-Diels-Alder-Epimerization reactions of readily available precursors enones 1a-i, arylaldehydes 2a-i and 1,3-indandione 3 to furnish highly substituted prochiral spiro[cyclohexane- 1,2'-indan]-1',3',4-triones 5a-i in a highly diastereoselective fashion with excellent yields. We demonstrate the first L-proline and pyrrolidine catalyzed epimerization reactions of trans-spiranes 6a-i to cis-spiranes 5a-i. Prochiral spiranes 5a-i are excellent starting materials for the synthesis of benzoannelated centropolyquinanes.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-41486