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Mechanistic study reveals enantioselective cyclization of hydroxylactams via thiourea-mediated anion abstraction, suggesting a broad paradigm for asymmetric hydrogen-bond donor catalysis.
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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Raheem et al. (2007) studied this question.
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