Recent Progress in the in situ Detrifluoro­acetylative Generation of Fluoro Enolates and Their Reactions with Electrophiles

Detrifluoroacetylative generation of fluoro enolates is an emerging area of high‐impact research. In this review article we provide, for the first time, a comprehensive and critical treatment of this subject. The reaction types reported to date include Mannich, aldol, and Michael addition and haloge...

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Published inEuropean journal of organic chemistry Vol. 2015; no. 29; pp. 6401 - 6412
Main Authors Mei, Haibo, Xie, Chen, Aceña, José Luis, Soloshonok, Vadim A., Röschenthaler, Gerd-Volker, Han, Jianlin
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.09.2015
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Aldol addtion
Asymmetric synthesis
Enolates
Fluorine
Haloform-type reactions
Mannich addition
Michael addition
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Abstract Detrifluoroacetylative generation of fluoro enolates is an emerging area of high‐impact research. In this review article we provide, for the first time, a comprehensive and critical treatment of this subject. The reaction types reported to date include Mannich, aldol, and Michael addition and halogenation reactions. These processes can be very successfully conducted in asymmetric fashion, in stoichiometric or catalytic mode. In general, these reactions allow for synthetically rather simple and practical installation of CF2, CHF, and quaternary CF structural units into various types of organic compounds. In particular, the overall scientific importance, as well as the potential influence of this methodology for the development of useful approaches to the preparation of pharmaceutically valuable compounds is highlighted. Attractive features such as operationally convenient, mild reaction conditions, remarkable substrate generality, and excellent stereochemical outcome bode well for widespread applications of this innovative and synthetically advanced approach. The high‐impact research in the new emerging area of detrifluoroacetylative in situ generation of fluoro enolates is comprehensively presented. The major reaction types featuring in this process include Mannich, aldol, and Michael addition and halogenation reactions. The scientific importance and practical potential of this methodology is highlighted and critically discussed.
AbstractList Detrifluoroacetylative generation of fluoro enolates is an emerging area of high‐impact research. In this review article we provide, for the first time, a comprehensive and critical treatment of this subject. The reaction types reported to date include Mannich, aldol, and Michael addition and halogenation reactions. These processes can be very successfully conducted in asymmetric fashion, in stoichiometric or catalytic mode. In general, these reactions allow for synthetically rather simple and practical installation of CF2, CHF, and quaternary CF structural units into various types of organic compounds. In particular, the overall scientific importance, as well as the potential influence of this methodology for the development of useful approaches to the preparation of pharmaceutically valuable compounds is highlighted. Attractive features such as operationally convenient, mild reaction conditions, remarkable substrate generality, and excellent stereochemical outcome bode well for widespread applications of this innovative and synthetically advanced approach. The high‐impact research in the new emerging area of detrifluoroacetylative in situ generation of fluoro enolates is comprehensively presented. The major reaction types featuring in this process include Mannich, aldol, and Michael addition and halogenation reactions. The scientific importance and practical potential of this methodology is highlighted and critically discussed.
Detrifluoroacetylative generation of fluoro enolates is an emerging area of high‐impact research. In this review article we provide, for the first time, a comprehensive and critical treatment of this subject. The reaction types reported to date include Mannich, aldol, and Michael addition and halogenation reactions. These processes can be very successfully conducted in asymmetric fashion, in stoichiometric or catalytic mode. In general, these reactions allow for synthetically rather simple and practical installation of CF 2 , CHF, and quaternary CF structural units into various types of organic compounds. In particular, the overall scientific importance, as well as the potential influence of this methodology for the development of useful approaches to the preparation of pharmaceutically valuable compounds is highlighted. Attractive features such as operationally convenient, mild reaction conditions, remarkable substrate generality, and excellent stereochemical outcome bode well for widespread applications of this innovative and synthetically advanced approach.
Detrifluoroacetylative generation of fluoro enolates is an emerging area of high-impact research. In this review article we provide, for the first time, a comprehensive and critical treatment of this subject. The reaction types reported to date include Mannich, aldol, and Michael addition and halogenation reactions. These processes can be very successfully conducted in asymmetric fashion, in stoichiometric or catalytic mode. In general, these reactions allow for synthetically rather simple and practical installation of CF2, CHF, and quaternary CF structural units into various types of organic compounds. In particular, the overall scientific importance, as well as the potential influence of this methodology for the development of useful approaches to the preparation of pharmaceutically valuable compounds is highlighted. Attractive features such as operationally convenient, mild reaction conditions, remarkable substrate generality, and excellent stereochemical outcome bode well for widespread applications of this innovative and synthetically advanced approach.
Author Aceña, José Luis
Xie, Chen
Mei, Haibo
Soloshonok, Vadim A.
Han, Jianlin
Röschenthaler, Gerd-Volker
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  givenname: Chen
  surname: Xie
  fullname: Xie, Chen
  organization: School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, 22 Hankou Road, Nanjing 210093, P. R. China, http://hysz.nju.edu.cn/yipan
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  givenname: José Luis
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– sequence: 4
  givenname: Vadim A.
  surname: Soloshonok
  fullname: Soloshonok, Vadim A.
  organization: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain
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  givenname: Gerd-Volker
  surname: Röschenthaler
  fullname: Röschenthaler, Gerd-Volker
  organization: Department of Life Sciences and Chemistry, Focus Area Health, Jacobs University Bremen, GmbH, P. O. Box 750561, 28725 Bremen, Germany
– sequence: 6
  givenname: Jianlin
  surname: Han
  fullname: Han, Jianlin
  email: hanjl@nju.edu.cn
  organization: School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, 22 Hankou Road, Nanjing 210093, P. R. China, http://hysz.nju.edu.cn/yipan
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2010; 12
2013; 3
1990; 55
2008; 37
2008; 108
2003; 59
2004; 6
2004; 5
2012; 10
1985; 24
2009; 11
1989; 30
1992; 8
2010; 21
2006; 24
2013; 52
2010; 352
2010; 110
2014; 16
2008; 359
2013; 355
1998; 92
2005; 70
2012; 23
1996; 255
2014; 12
2003; 44
2014; 97
2015; 51
2015; 54
1996
1995
2011; 76
2002; 4
1998; 63
2008; 51
2011; 8
2011; 133
1999
2011; 9
2015; 115
2006; 45
2015; 357
2013; 78
1934; 15
2005; 127
2008; 49
2005; 7
1988; 24
1997; 38
2012; 48
1989; 59
1990; 112
2012; 44
1955; 77
2012; 41
2006; 71
2013; 25
2004; 125
1952; 74
2011; 13
1996; 37
2012; 53
1960; 82
2015; 172
2014; 4
2013; 11
2002; 43
2013; 155
1994; 35
2008; 64
2006; 127
2014; 165
2003; 125
2014; 50
2014; 55
2005; 34
2003; 121
2014; 167
1996; 7
1997; 62
2012; 143
2007; 129
2004; 104
2015; 5
2007; 128
2013; 49
2011
2008; 18
2002; 35
2006; 8
1953
1996; 52
2005
1999; 64
2002
2001; 66
2012; 77
2014; 114
2007; 356
2015; 25
2003; 68
2010; 131
2009; 7
2001; 3
2015
2014
2013
2009; 1
1994; 5
2007; 46
1968; 33
2007; 48
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Snippet Detrifluoroacetylative generation of fluoro enolates is an emerging area of high‐impact research. In this review article we provide, for the first time, a...
Detrifluoroacetylative generation of fluoro enolates is an emerging area of high-impact research. In this review article we provide, for the first time, a...
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SubjectTerms Aldol addtion
Asymmetric synthesis
Enolates
Fluorine
Haloform-type reactions
Mannich addition
Michael addition
Title Recent Progress in the in situ Detrifluoro­acetylative Generation of Fluoro Enolates and Their Reactions with Electrophiles
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https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.201500787
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Volume 2015
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