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

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 u...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 48; no. 41; pp. 7604 - 7607
Main Authors Han, Xiao, Kwiatkowski, Jacek, Xue, Feng, Huang, Kuo-Wei, Lu, Yixin
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 28.09.2009
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric synthesis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Esters - chemistry
fluorination
Fluorine - chemistry
Ketones - chemistry
Mannich reaction
Molecular Conformation
Molecular Structure
organocatalysis
Physical Sciences
quaternary stereocenters
Science & Technology
Thiourea - chemistry
Tryptophan - chemistry
ACTIVATION
DIRECT CONJUGATE ADDITION
ENANTIOSELECTIVE FLUORINATION
MALONATE
fluorination
CARBONYL-COMPOUNDS
BETA-KETO-ESTERS
HALOGENATION
MICHAEL ADDITION
organocatalysis
asymmetric synthesis
quaternary stereocenters
Mannich reaction
NITROALKENES
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Summary: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).
Bibliography:National University of Singapore
ark:/67375/WNG-F32B55NS-G
istex:6A3373179EBA6F36ED163CC1B1D75AC4F742C177
We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.
ArticleID:ANIE200903635
Ministry of Education (MOE) of Singapore - No. R-143-000-362-112
We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R‐143‐000‐362‐112) for generous financial support.
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SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200903635