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October 17, 2007Journal of the American Chemical Society548 citations

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

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IRIzzat T. RaheemPTParvinder S. ThiaraEPEmily A. Peterson

Key Points

  • Develop an enantioselective Pictet−Spengler-type cyclization of tryptamine-derived hydroxylactams and investigate the catalytic mode of action.
  • Carried out asymmetric cyclizations of tryptamine-derived hydroxylactams using chiral thiourea catalysts to form indolizinone and quinolizinone frameworks.
  • Investigated catalytic reaction pathways through systematic substituent and counterion effect experiments.
  • Yielded highly enantioenriched indolizinone and quinolizinone heterocycles under mild thiourea-catalyzed conditions.
  • Demonstrated that the reaction operates through rate-limiting anion abstraction and recognition enabled by hydrogen-bond donor catalysis.

Abstract

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.

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Cite This Study

Raheem et al. (2007) studied this question.

synapsesocial.com/papers/69d6a6e539aaaf0da5ab30cchttps://doi.org/10.1021/ja076179w
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