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South African Journal of Chemistry

versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350

S.Afr.j.chem. (Online) vol.65  Durban  2012

 

RESEARCH ARTICLE

 

Comparison of tetrahydroisoquinoline (TIQ) thiazole and oxazoline ligands for asymmetric Henry reactions

 

 

Sunayna S. PawarI; Sai Kumar ChakkaII; Pher G. AnderssonII, III; Hendrik G. KrugerII; Glenn E.M. MaguireII; Thavendran GovenderI, *

ISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Westville Campus, Durban, 4000, South Africa
IISchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Durban, 4000, South Africa
IIIDepartment of Biochemistry and Organic Chemistry, Uppsala University, SE-751 23, Uppsala, Sweden

 

 


ABSTRACT

A series of novel C1 symmetric thiazole ligands with a tetrahydroisoquinoline (TIQ) backbone were synthesized. Their application in the catalytic asymmetric Henry reaction was investigated with comparison to a corresponding TIQ oxazoline ligand. The Cu(II)-oxazoline complex was more reactive and furnished moderate enantioselectivities up to 61:36 (syn:anti) with 75:25 diastereomeric excess, while the Cu(II)-thiazole complexes had lower selectivity. This is the first example where a direct comparison between an N, N-type thiazole and oxazoline ligands has been studied.

Keywords: Tetrahydroisoquinoline, thiazole, oxazoline, Henry reaction, enantioselectivity


 

 

Full text available only in PDF format.

 

Acknowledgements

This work was supported by the National Research Foundation (South Africa, GUN 2073251, GUN 58505), SA/Swedish Research Links Programme grant and Aspen Pharmacare, SA.

 

References

1 T.P. Yoon and E.N. Jacobsen, Science, 2003, 299, 1691-1693.         [ Links ]

2 L. Van, P. Paul, W.N.M. Kamer and C.J. Claver, Chem. Rev., 2011, 111, 2077-2118.         [ Links ]

3 P.F. Teng C.S. Tsang H.L. Yeung W.L. Wong, H.L. Kwong and I.D. Williams, J. Organomet. Chem., 2006, 691, 2237-2244.         [ Links ]

4 P.F. Teng, C.S. Tsang, H.L. Yeung, W.L. Wong, W.T. Wong and H.L. Kwong, J. Organomet. Chem., 2006, 691, 5664-5672.         [ Links ]

5 M.N. Birkholz, N.V Dubrovina, I.A. Shuklov, J. Holz, R. Paciello, C. Waloch, B. Breit and A. Borner, Tetrahedron: Asymmetry, 2007, 18, 2055-2060.         [ Links ]

6 Z.B. Dong, B. Liu, C. Fang and J.S. Li, J. Organomet. Chem., 2008, 693, 17-22.         [ Links ]

7 P. Cheruku, A. Paptchikhine, M. Ali, J.M. Neudorfl and P.G. Andersson, Org. Biomol. Chem., 2008, 6, 366-373.         [ Links ]

8 K. Kallstrom and P.G. Andersson, Tetrahedron Lett., 2006, 47, 7477-7480.         [ Links ]

9 C. Hedberg K. Kallstrom, P. Brandt, L.K. Hansen and P.G. Andersson, J. Am. Chem. Soc., 2006, 128, 2995-3001.         [ Links ]

10 Q. Li, A. Paptchikhine, T. Govender and P.G. Andersson, Tetrahedron-Asymmetry, 2010, 21, 1328-1333.         [ Links ]

11 Mazuela, A. Paptchikhine, P. Tolstoy, O. Pamies, M. Dieguez and P.G. Andersson, Chem. Eur. J, 2010, 16, 620-638.         [ Links ]

12 P. Koranta, K.Kallstrom and P.G. Andersson, Adv. Synth. Catal., 2007, 349, 2595-2602.         [ Links ]

13 P. Kaukoranta, M. Engman, C. Hedberg, J. Bergquist and P.G. Andersson, Adv. Synth. Catal, 2008, 350, 1168-1176.         [ Links ]

14 U. Bremberg, F. Rahm and C. Moberg, Tetrahedron:Asymmetry, 1998, 9, 3437-3443.         [ Links ]

15 U. Bremberg, M. Larhed, C. Moberg and A. Hallberg, J. Org. Chem., 1999, 64, 1082-1083.         [ Links ]

16 K. Nordstrom, E. Macedo and C. Moberg, J. Org. Chem., 1997, 62, 1604-1609.         [ Links ]

17 T. Akiyama, J. Itoh and K. Fuchibe, Adv. Synth. Catal., 2006, 348, 999-1010.         [ Links ]

18 G.K. Friestad and A.K. Mathies, Tetrahedron, 2007, 63, 2541-2569.         [ Links ]

19 S. Gao, G. Xi, N. Li, C. Wang and J. Ma, Chin. J. Org. Chem., 2010, 30, 1811-1819.         [ Links ]

20 R. Gomez Arrayas and J.C. Carretero, Chem. Soc. Rev., 2009, 38, 1940-1948.         [ Links ]

21 C. Palomo, M. Oiarbide and R. Lopez, Chem. Soc. Rev., 2009, 38, 632-653.         [ Links ]

22 M. Petrini and E. Torregiani, Synthesis-Stuttgart, 2007, 159-186.         [ Links ]

23 Y. Wei, B.-L. Zhang, P. Liu, W. He and S.-Y. Zhang, Mini-Rev. Org. Chem., 2011, 8, 66-90.         [ Links ]

24 S.M. Weinreb and R.K. Orr, Synthesis-Stuttgart, 2005, 1205-1227.         [ Links ]

25 Y.Q. Ji, G. Qi, and Z.M.A. Judeh, Eur. J. Org. Chem., 2011, 4892-4898.         [ Links ]

26 Q. Ji, G. Qi and Z.M.A. Judeh, Tetrahedron:Asymmetry, 2011, 22, 929-935.         [ Links ]

27 Q.J. Yao and Z.M.A. Judeh, Tetrahedron, 2011, 67, 4086-4092.         [ Links ]

28 R.B. Kawthekar, S.K. Chakka, V Francis, P.G. Andersson, H.G. Kruger and G.E.M. Maguire, T. Govender, Tetrahedron: Asymmetry, 2010, 21, 846-852.         [ Links ]

29 J.S. Gary, L. Grunewald and J.A.A. Monn, J. Med. Chem., 1998, 31, 824-830.         [ Links ]

30 Naicker, K. Petzold, T. Singh, P.I. Arvidsson, H.G. Kruger, G.E.M. Maguire, T. Govender, Tetrahedron: Asymmetry, 2010, 21, 2859-2867.         [ Links ]

31 C. Craig, Z.M.A. Judeh and R.W. Read, Aust. J. Chem., 2002, 55, 733-736.         [ Links ]

32 T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink and H. Griengl, Angew. Chem. Int. Ed., 2006, 45, 3454-3456.         [ Links ]

33 D.A. Evans, D. Seidel, M. Rueping, H.W. Lam, J.T. Shaw and C.W. Downey, J. Am. Chem. Soc., 2003, 125, 12692-12693.         [ Links ]

34 R. Kowalczyk and J. Skarzewski, Tetrahedron: Asymmetry, 2009, 20, 2467-2473.         [ Links ]

35 S. Jammi, P. Saha, S. Sanyashi, S. Sakthivel and T. Punniyamurthy, Tetrahedron, 2008, 64, 11724-11731.         [ Links ]

36 H.Y. Kim and K. Oh, Org. Lett., 2009, 11, 5682-5685.         [ Links ]

37 A. Noole, K. Lippur, A. Metsala, M. Lopp and T. Kanger, J. Org. Chem., 2010, 75, 1313-1316.         [ Links ]

38 S.K. Ginotra and V.K. Singh, Org. Biomol. Chem., 2007, 5, 3932-3937.         [ Links ]

 

 

Received 21 October 2011
Revised 29 November 2011
Accepted 18 January 2012

 

 

Submitted by invitation to celebrate 2011 the 'International Year of Chemistry'.
* To whom correspondence should be addressed. E-mail: govenderthav@ukzn.ac.za

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