Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams:  H-Bond Donor Catalysis by Anion Binding

Highly enantioenriched indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiou...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-11, Vol.129 (44), p.13404-13405
Main Authors: Raheem, Izzat T, Thiara, Parvinder S, Peterson, Emily A, Jacobsen, Eric N
Format: Article
Language:English
Subjects:
Anions - chemistry
Binding Sites
Catalysis
Cyclization
Hydrogen Bonding
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Stereoisomerism
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Summary:Highly enantioenriched indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiourea.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja076179w