Synlett 2019; 30(08): 869-874
DOI: 10.1055/s-0037-1612078
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© Georg Thieme Verlag Stuttgart · New York

Asymmetric Transformations of α-Hydroxy Enamides Catalyzed by Chiral Brønsted Acids

Subramani Rajkumar ◊
,
Jiawen Wang ◊
,
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, P. R. of China   Email: yangxy1@shanghaitech.edu.cn
› Author Affiliations
We gratefully acknowledge financial support from NSFC (Grant No. 21702138), the Shanghai Pujiang Program, Thousand Talents Plan youth program, and ShanghaiTech University startup funding.
Further Information

Publication History

Received: 27 November 2018

Accepted after revision: 20 December 2018

Publication Date:
22 January 2019 (online)

◊ These authors contributed equally to this work.

Dedicated to Professor Yong-Zheng Hui on the occasion for his 80th birthday

Abstract

2-Aminoallyl cations are reactive intermediates that undergo diverse reactions, such as cycloadditions, direct nucleophilic additions, Nazarov electrocyclizations, and rearrangements. We review recent development in asymmetric catalytic reactions (nucleophilic additions and Nazarov electrocyclizations) based on chiral counteranion-paired 2-aminoallyl cation intermediates generated through activation of α-hydroxy enamides in the presence of chiral Brønsted acid catalysts. With an understanding of their asymmetric catalysis modes and mechanisms, we expect more asymmetric catalytic reactions will be developed on the basis of this strategy in the near future.

 
  • References

    • 1a Harmata M. Acc. Chem. Res. 2001; 34: 595
    • 1b Harmata M. Chem. Commun. 2010; 46: 8886
    • 1c Li H, Wu J. Synthesis 2015; 47: 22
    • 1d Lohse AG, Hsung RP. Chem. Eur. J. 2011; 17: 3812
    • 2a Harmata M, Ghosh SK, Hong X, Wacharasindhu S, Kirchhoefer P. J. Am. Chem. Soc. 2003; 125: 2058
    • 2b Huang J, Hsung RP. J. Am. Chem. Soc. 2005; 127: 50
    • 2c Topinka M, Zawatzky K, Barnes CL, Welch CJ, Harmata M. Org. Lett. 2017; 19: 4106
    • 2d Villar L, Uria U, Martínez JI, Prieto L, Reyes E, Carrillo L, Vicario JL. Angew. Chem. Int. Ed. 2017; 56: 10535
    • 3a Vander Wal MN, Dilger AK, MacMillan DW. C. Chem. Sci. 2013; 4: 3075
    • 3b Liu C, Oblak EZ, Vander Wal MN, Dilger AK, Almstead DK, MacMillan DW. C. J. Am. Chem. Soc. 2016; 138: 2134
    • 4a Kende AS, Huang H. Tetrahedron Lett. 1997; 38: 3353
    • 4b Prié G, Prévost N, Twin H, Fernandes SA, Hayes JF, Shipman M. Angew. Chem. Int. Ed. 2004; 43: 6517
    • 4c Kim H, Ziani-Cherif C, Oh J, Cha JK. J. Org. Chem. 1995; 60: 792
    • 4d Stoll AH, Blakey SB. Chem. Sci. 2011; 2: 112
    • 4e Schmid R, Schmid H. Helv. Chim. Acta 1974; 57: 1883
    • 4f De Kimpe N, Stevens C. Tetrahedron 1990; 46: 6753
    • 5a Bonderoff SA, Grant TN, West FG, Tremblay M. Org. Lett. 2013; 15: 2888
    • 5b Ma Z.-X, He S, Song W, Hsung RP. Org. Lett. 2012; 14: 5736
  • 6 Saputra MA, Dange NS, Cleveland AH, Malone JA, Fronczek FR, Kartika R. Org. Lett. 2017; 19: 2414
  • 7 Schlegel M, Schneider C. J. Org. Chem. 2017; 82: 5986
  • 8 Griffin K, Montagne C, Hoang CT, Clarkson GJ, Shipman M. Org. Biomol. Chem. 2012; 10: 1032
    • 9a Feast GC, Page LW, Robertson J. Chem. Commun. 2010; 46: 2835
    • 9b Stoll AH, Blakey SB. J. Am. Chem. Soc. 2010; 132: 2108
    • 10a Lacour J, Hebbe-Viton V. Chem. Soc. Rev. 2003; 32: 373
    • 10b Lacour J, Moraleda D. Chem. Commun. 2009; 7073
    • 10c Phipps RJ, Hamilton GL, Toste FD. Nat. Chem. 2012; 4: 603
    • 10d Brak K, Jacobsen EN. Angew. Chem. Int. Ed. 2013; 52: 534
    • 10e Mahlau M, List B. Angew. Chem. Int. Ed. 2013; 52: 518
  • 11 Akiyama T, Itoh J, Yokota K, Fuchibe K. Angew. Chem. Int. Ed. 2004; 43: 1566
  • 12 Uraguchi D, Terada M. J. Am. Chem. Soc. 2004; 126: 5356
    • 13a Akiyama T. Chem. Rev. 2007; 107: 5744
    • 13b Terada M. Synthesis 2010; 1929
    • 13c Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
    • 13d Li X, Song Q. Chin. Chem. Lett. 2018; 29: 1181
  • 14 Rajkumar S, Wang J, Zheng S, Wang D, Ye X, Li X, Peng Q, Yang X. Angew. Chem. Int. Ed. 2018; 57: 13489
  • 15 Saputra MA, Nepal B, Dange NS, Du P, Fronczek FR, Kumar R, Kartika R. Angew. Chem. Int. Ed. 2018; 57: 15558
  • 16 Jin J, Zhao Y, Gouranourimi A, Ariafard A, Chan PW. H. J. Am. Chem. Soc. 2018; 140: 5834