Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio- and Diastereoselective Guanidine-Catalyzed Addition of Fluorocarbon Nucleophiles

The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was dem...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 20; pp. 3627 - 3631
Main Authors Jiang, Zhiyong, Pan, Yuanhang, Zhao, Yujun, Ma, Ting, Lee, Richmond, Yang, Yuanyong, Huang, Kuo-Wei, Wong, Ming Wah, Tan, Choon-Hong
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
Chemistry
Chemistry, Multidisciplinary
fluorine
guanidine
Michael addition
Physical Sciences
Science & Technology
transition states
Michael addition
ASYMMETRIC FLUORINATION
ELECTROPHILIC FLUORINATION
ENANTIOSELECTIVE FLUORINATION
1,3-DICARBONYL COMPOUNDS
asymmetric catalysis
BETA-KETO-ESTERS
guanidine
CINCHONA ALKALOIDS
transition states
MANNICH REACTIONS
BICYCLIC GUANIDINE
ALPHA-FLUORINATION
fluorine
CONJUGATE ADDITION
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Summary:The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.
Bibliography:http://dx.doi.org/10.1002/anie.200900964
This work was supported by ARF grants (R‐143‐000‐337‐112 and R‐143‐000‐342‐112) from the National University of Singapore.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900964