Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons

We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Brønsted acid. The indole–pyrone add...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 136; no. 39; pp. 13614 - 13617
Main Authors Yeung, Charles S, Ziegler, Robert E, Porco, John A, Jacobsen, Eric N
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.10.2014
Amer Chemical Soc
Subjects
Alkaloids
Alkaloids - chemical synthesis
Alkaloids - chemistry
Bearing
Carbon
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Communication
Indoles
Indoles - chemistry
Molecular Structure
Natural products
Physical Sciences
Pyrones - chemistry
Science & Technology
Stereoisomerism
Stereoselectivity
Thiourea - chemistry
ANION-BINDING CATALYSIS
ASYMMETRIC-SYNTHESIS
COOPERATIVE CATALYSIS
PRACTICAL ROUTE
ACID
CONCISE TOTAL-SYNTHESIS
ALPHA-ARYLATION
C3-QUATERNARY INDOLENINES
PICTET-SPENGLER REACTIONS
ALKENE CYCLOADDITIONS
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Summary:We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Brønsted acid. The indole–pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine.
Bibliography:NIH RePORTER
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja508523g