Asymmetric Friedel–Crafts Alkylation Reaction in the Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters

Hao Wu; Ren-Rong Liu; Yi-Xia Jia

doi:10.1055/s-0033-1340318

Synlett, Table of Contents

Synlett 2014; 25(4): 457-460
DOI: 10.1055/s-0033-1340318

synpacts

Asymmetric Friedel–Crafts Alkylation Reaction in the Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters

Hao Wu

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Fax: +86(571)88320544 Email: yxjia@zjut.edu.cn

,

Ren-Rong Liu

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Fax: +86(571)88320544 Email: yxjia@zjut.edu.cn

,

Yi-Xia Jia*

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Fax: +86(571)88320544 Email: yxjia@zjut.edu.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

Construction of all-carbon quaternary stereocenter by asymmetric Friedel–Crafts alkylation reaction remains a significant challenge. By the introduction of CF₃ group at the β-position of nitroalkene, a highly enantioselective Friedel–Crafts reaction of indoles with β-CF₃-β-substituted nitroalkenes was achieved using Ni(ClO₄)₂-bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereogenic centers in good yields and excellent enantioselectivities.

Key words

alkylation - asymmetric catalysis - fluorine - indole - nickel

Full Text

References

References

For a book, see:

1a Bandini M, Umani-Ronchi A. Catalytic Asymmetric Friedel–Crafts Alkylations . Wiley-VCH; Weinheim: 2009

For reviews, see:

1b Poulsen TB, Jørgensen KA. Chem. Rev. 2008; 108: 2903
1c You S.-L, Cai Q, Zeng M. Chem. Soc. Rev. 2009; 38: 2190
1d Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
1e Terrasson V, Figueiredo RM, Campagne JM. Eur. J. Org. Chem. 2010; 2635

2a Trost BM, Jiang C. Synthesis 2006; 369
2b Hawner C, Alexakis A. Chem. Commun. 2010; 46: 7295

3a Banwell MG, Beck DA. S, Willis AC. ARKIVOC 2006; (iii): 163
3b Lyzwa D, Dudzinski K, Kwiatkowski P. Org. Lett. 2012; 14: 1540

4a Arai T, Yamamoto Y, Awata A, Kamiya K, Ishibashi M, Arai MA. Angew. Chem. Int. Ed. 2013; 52: 2486
4b Liu R, Zhang J. Org. Lett. 2013; 15: 2266

5a Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Wiley-VCH; Weinheim: 2004
5b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
5c Bégué J.-P, Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine . Wiley-VCH; Weinheim: 2008
5d Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology. Wiley; Chichester: 2009
5e Lin G.-Q, You Q.-D, Cheng J.-F. Chiral Drugs: Chemistry and Biological Action . Wiley-VCH; Hoboken: 2011

For recent reviews, see:

6a Shibata N, Mizuta S, Kawai H. Tetrahedron: Asymmetry 2008; 19: 2633
6b Ma J.-A, Cahard D. Chem. Rev. 2008; 108: PR1
6c Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455

7a Huang Y, Tokunaga E, Suzuki S, Shiro M, Shibata N. Org. Lett. 2010; 12: 1136
7b Blay G, Fernandez I, Munoz MC, Pedro JR, Vila C. Chem. Eur. J. 2010; 16: 9117
7c Lin J.-H, Xiao J.-C. Eur. J. Org. Chem. 2011; 4536
7d Wang W, Lian X, Chen D, Liu X, Lin L, Feng X. Chem. Commun. 2011; 47: 7821
7e Wen L, Shen Q, Wan X, Lu L. J. Org. Chem. 2011; 76: 2282
7f Shibatomi K, Narayama A, Abe Y, Iwasa S. Chem. Commun. 2012; 48: 7380

8 Gao J.-R, Wu H, Xiang B, Yu W.-B, Han L, Jia Y.-X. J. Am Chem. Soc. 2013; 135: 2983

9a Wu J, Mampreian DM, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 4584
9b Lu H.-H, Zhang F.-G, Meng X.-G, Duan S.-W, Xiao W.-J. Org. Lett. 2009; 11: 3946
9c Zhang F.-G, Yang Q.-Q, Xuan J, Lu H.-H, Duan S.-W, Chen J.-R, Xiao W.-J. Org. Lett. 2010; 12: 5636