Services on Demand
Article
Indicators
Related links
- Cited by Google
- Similars in Google
Share
South African Journal of Chemistry
On-line version ISSN 1996-840X
Print version ISSN 0379-4350
S.Afr.j.chem. (Online) vol.62 Durban 2009
RESEARCH ARTICLE
The evaluation of novel camphor-derived pyridyl ligands as catalysts in the asymmetric Diels-Alder reaction of cyclopentadiene with 3-acryloyl-2-oxazolidinone
Grant A. BoyleI; Thavendran GovenderII; Hendrik G. KrugerI; Tricia NaickerI; Glenn E.M. MaguireI
ISchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
IISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa
ABSTRACT
A series of camphor-derived pyridyl ligands were evaluated in the Diels-Alder reaction of 3-acryloyl-2-oxazolidinone 1 with cyclopentadiene 2. High yields with good endo:exo selectivity, but only moderate enantioselectivities (43 % ee), were obtained. The structures of the copper (II) complexes of the ligands were calculated using ONIOM density functional theory and the results suggest that chiral induction to the alkene functional group is indeed lacking. This explains the moderate experimental selectivities obtained.
Keywords: Camphor ligands, asymmetric catalysis, Diels-Alder cycloaddition, computational modelling
Full text available only in PDF format.
Acknowledgements
This work was supported by grants from the National Research Foundation, GUN 2046819 (South Africa), Aspen Pharmacare and the University of KwaZulu-Natal.
References
1 P.I. Arvidsson, T. Govender, H.G. Kruger, G.E.M. Maguire and T. Naicker, S. Afr. J. Chem., 2009, 62, 60-66. [ Links ]
2 G.A. Boyle, T. Govender, H.G. Kruger and G.E.M. Maguire, S. Afr. J. Chem., 2009, 62, 113-123. [ Links ]
3 G.A. Boyle, T. Govender, H.G. Kruger and G.E.M. Maguire, S. Afr. J. Chem., 2009, 62, 124-128. [ Links ]
4 F. Friguelli and A. Taticchi (eds.), The Diels-Alder Reaction: Selected Practical Methods, John Wiley & Sons, Chichester, UK, 2002. [ Links ]
5 J.D. Morrison and H.S. Mosher (eds), Asymmetric Organic Reactions, Prentice Hall, Englewood Cliffs, NJ, USA, 1971. [ Links ]
6 L.A. Paquette (ed.), Asymmetric Synthesis, Academic Press, New York, NY, USA, 1984. [ Links ]
7 G. Helmchen, R. Karge and J. Weetman (eds.), Modern Synthetic Methods, Springer-Verlag, New York, NY, USA, 1986. [ Links ]
8 H.B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007-1019. [ Links ]
9 O. Diels and K. Alder, Justus Liebigs Ann. Chem, 1928, 460, 98-122. [ Links ]
10 M.M. Guseinov, M.I. Akhmedov and E.G. Mamedov, Chem. Abstr, 1976, 85, 176295z. [ Links ]
11 J.M. Takacs, E.C. Lawson, M.J. Reno, M.A. Youngman and D.A. Quincy, Tetrahedron: Asymmetry, 1997, 8, 3073-3078. [ Links ]
12 D.A. Evans, T. Lectka and S.J. Miller, Tetrahedron Lett., 1993, 34, 7027-7030. [ Links ]
13 D.A. Evans, S.J. Miller and T. Lectka, J. Am. Chem. Soc., 1993, 115, 6460-6461. [ Links ]
14 D.A. Evans, J.A. Murry, P.V Matt, R.D. Norcross and S.J. Miller, Angew. Chem., Int. Ed. Engl., 1995, 34, 798-800. [ Links ]
15 D.A. Evans, M.C. Kozlowski and J.S. Tedrow, Tetrahedron Lett., 1996, 37, 7481-7484. [ Links ]
16 A.K. Ghosh, H. Cho and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 3687-3691. [ Links ]
17 D.A. Evans, D.M. Barnes, J.S. Johnson, T. Lectka, P. von Matt, S.J. Miller, J.A. Murry, R.D. Norcross, E.A. Shaughnessy and K.R. Campos, J. Am. Chem. Soc., 1999, 121, 7582-7594. [ Links ]
18 D.A. Evans, S.J. Miller, T. Lectka and P. von Matt, J. Am. Chem. Soc., 1999, 121, 7559-7573. [ Links ]
19 K. Hiroi and K. Watanabe, Tetrahedron: Asymmetry, 2001, 12, 3067-3071. [ Links ]
20 S. Barroso, G. Blay, L. Cardona and J.R. Pedro, Synlett, 2007, 17, 2659-2662. [ Links ]
21 H. He, B.-J. Pei, H.-H. Chou, T. Tian, W.-H. Chan and A.WM. Lee, Org. Lett., 2008, 10, 2421-2424. [ Links ]
22 G. Chelucci, Chem. Soc. Rev., 2006, 35, 1230-1243. [ Links ]
23 G. Desimoni, G. Faita and K.A. Jorgensen, Chem. Rev., 2006, 106, 3561-3651. [ Links ]
24 P.Y. Bruice, Organic Chemistry, 4th edn., Prentice Hall, Englewood Cliffs, NJ, USA, 2004. [ Links ]
25 C. Sivasankar, N. Sadhukhan, J.K. Bera and A.G. Samuelson, New J. Chem., 2007, 31, 385-393. [ Links ]
26 G. Drudis-Solé, F. Maseras, A. Lledós, A. Vallribera and M. Moreno-Manas, Eur. J. Org. Chem., 2008, 33, 5614-5621. [ Links ]
27 A.E. Clark, S. Bhattacharrya and J.M. Zaleski, Inorg. Chem., 2009, 48, 3926-3933. [ Links ]
28 Y.-H. Lam, P. H.-Y. Cheong, J.M.B. Mata, S.J. Stanway, V.R. Gouverneur and K.N. Houk, J. Am. Chem. Soc., 2009, 131, 1947-1957. [ Links ]
29 M.N. Paddon-Row, C.D. Anderson and K.N. Houk, J. Org. Chem., 2009, 74, 861-868. [ Links ]
Received 3 March 2009
Revised 25 May 2009
Accepted 28 May 2009
* To whom correspondence should be addressed. E-mail: kruger@ukzn.ac.za