Synlett 2014; 25(12): 1633-1637
DOI: 10.1055/s-0033-1341160
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© Georg Thieme Verlag Stuttgart · New York

Desymmetrization as a Strategy in Asymmetric Halocyclization Reactions

Ulrich Hennecke*
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany   Fax: +49(251)8336523   Email: ulrich.hennecke@uni-muenster.de
,
Michael Wilking
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany   Fax: +49(251)8336523   Email: ulrich.hennecke@uni-muenster.de
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Further Information

Publication History

Received: 22 February 2014

Accepted after revision: 17 March 2014

Publication Date:
10 April 2014 (online)

Abstract

Halocyclization reactions such as halolactonization are powerful synthetic methods for the functionalization of alkenes and alkynes. However, asymmetric versions were thought of as difficult reactions and only recently have new asymmetric, organocatalytic halocyclization methods been reported. Herein, we examine a specific strategy for asymmetric halocyclization reactions, desymmetrizing cyclizations, and highlight recent contributions in this area.

 
  • References

  • 2 Castellanos A, Fletcher SP. Chem. Eur. J. 2011; 17: 5766
    • 3a Tan CK, Zhou L, Yeung Y.-Y. Synlett 2011; 1335
    • 3b Hennecke U. Chem. Asian J. 2012; 7: 456
    • 3c Denmark SE, Kuester WE, Burk MT. Angew. Chem. Int. Ed. 2012; 51: 10938
    • 3d Murai K, Fujioka H. Heterocycles 2013; 87: 763
    • 3e Tan CK, Yeung Y.-Y. Chem. Commun. 2013; 49: 7985
    • 3f Tripathi CB, Mukherjee S. Synlett 2014; 25: 163
  • 4 Takano S, Murakata C, Imamura Y, Tamura N, Ogasawara K. Heterocycles 1981; 16: 1291
  • 5 Hart DJ, Huang H.-C, Krishnamurthy R, Schwartz T. J. Am. Chem. Soc. 1989; 111: 7507
  • 6 Fuji K, Manabu N, Naniwa Y, Kawabata T. Tetrahedron Lett. 1990; 31: 3175
    • 7a Yokomatsu T, Iwasawa H, Shibuya S. J. Chem. Soc., Chem. Commun. 1992; 728
    • 7b Yokomatsu T, Iwasawa H, Shibuya S. Tetrahedron Lett. 1992; 33: 6999
  • 8 Kitagawa O, Momose S, Fushimi Y, Taguchi T. Tetrahedron Lett. 1999; 40: 8827
    • 9a Najdi S, Reichlin D, Kurth MJ. J. Org. Chem. 1990; 55: 6241
    • 9b Moon H.-S, Eisenberg SW. E, Wilson ME, Schore NE, Kurth MJ. J. Org. Chem. 1994; 59: 6504
    • 9c Hajra S, Bhowmick M, Karmakar A. Tetrahedron Lett. 2005; 46: 3073
    • 9d Hajra S, Karmakar A, Bhowmick M. Tetrahedron 2005; 61: 2279
    • 10a Fujioka H, Kitagawa H, Matsunaga N, Nagatomi Y, Kita Y. Tetrahedron Lett. 1996; 37: 2245
    • 10b Fujioka H, Kitagawa N, Nagatomi Y, Kita Y. J. Org. Chem. 1996; 61: 7309
    • 10c For a review, see: Fujioka H. Synlett 2012; 825
  • 11 Fujioka H, Ohba Y, Hirose H, Murai K, Kita Y. Angew. Chem. Int. Ed. 2005; 44: 734
  • 12 Fujioka H, Kotoku N, Sawama Y, Nagatomi Y, Kita Y. Tetrahedron Lett. 2002; 43: 4825
  • 13 For a review, see: Kitagawa O, Taguchi T. Synlett 1999; 1191
  • 14 Kitagawa O, Hanano T, Tanabe K, Shiro M, Taguchi T. J. Chem. Soc., Chem. Commun. 1992; 1005
    • 15a Inoue T, Kitagawa O, Kurumizawa S, Ochiai O, Taguchi T. Tetrahedron Lett. 1995; 36: 1479
    • 15b Inoue T, Kitagawa O, Saito A, Taguchi T. J. Org. Chem. 1997; 62: 7384
    • 16a Whitehead DC, Yousefi R, Jaganathan A, Borhan B. J. Am. Chem. Soc. 2010; 132: 3298
    • 16b Zhou L, Tan CK, Jiang X, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 15474
    • 16c Murai K, Matsushita T, Nakamura A, Fukushima S, Shimura M, Fujioka H. Angew. Chem. Int. Ed. 2010; 49: 9174
    • 16d Veitch GE, Jacobsen EN. Angew. Chem. Int. Ed. 2010; 49: 7332
  • 17 Paull D, Fang C, Donald JR, Pansick AD, Martin SF. J. Am. Chem. Soc. 2012; 134: 11128
  • 18 Ikeuchi K, Ido S, Yoshimura S, Asakawa T, Inai M, Hamashima Y, Kan T. Org. Lett. 2012; 14: 6016
  • 19 Dobish MC, Johnston JN. J. Am. Chem. Soc. 2012; 134: 6068
  • 20 Wilking M, Mück-Lichtenfeld C, Daniliuc CG, Hennecke U. J. Am. Chem. Soc. 2013; 135: 8133
  • 21 Hennecke U, Müller CH, Fröhlich R. Org. Lett. 2011; 13: 860
  • 22 El-Qisairi AK, Qaseer HA, Katsigras G, Lorenzi P, Trivedi U, Tracz S, Hartman A, Miller JA, Henry PM. Org. Lett. 2003; 5: 439