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Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan-Derived Bifunctional Thiourea Catalyst

Authors

  • Xiao Han,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
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  • Jacek Kwiatkowski,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
    2. NUS Graduate School for Integrative Sciences and Engineering (Singapore)
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  • Feng Xue Prof. Dr.,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
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  • Kuo-Wei Huang Prof. Dr.,

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
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  • Yixin Lu Prof. Dr.

    1. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
    2. Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore (Singapore)
    3. NUS Graduate School for Integrative Sciences and Engineering (Singapore)
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Errata

This article is corrected by:

  1. Errata: Corrigendum: Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan-Derived Bifunctional Thiourea Catalyst Volume 50, Issue 12, 2664, Article first published online: 8 March 2011

  • We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.

Abstract

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Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β-lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

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