A modified tridentate pyridine bisoxazoline (pybox) ligand, possessing gem-diphenyl substitution at C-5 of the oxazoline rings, has been proved to be a very efficient ligand for enantioselective allylic oxidation, one-pot three-component synthesis of propargy-amines, and Friedel–Crafts alkylation of various aromatic compounds. We have shown that a 5',5'-diphenyl grouping in the oxazoline rings of chiral ligands is crucial for higher reaction rates as well as enhanced enantioselectivity.
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Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Stohner, Jürgen
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Chiral 2,6-bis(5',5'-diphenyloxazoline)pyridine as an efficient ligand for asymmetric catalysis
Pradeep K. Singh / Vinod K. Singh
Published Online: 2012-06-05 | DOI: https://doi.org/10.1351/PAC-CON-11-10-16
Free Access
Keywords: 2,6-bis(5',5'-diphenyloxazoline)pyridine; allylic oxidation; asymmetric catalysis; enantioselective reaction; Friedel–Crafts reaction; propargylamine; pyridine-bisoxazoline gem-diphenyl (pybox-diph)
Conference
International Conference on Heterocyclic Chemistry (ICHC-23), International Congress on Heterocyclic Chemistry, ICHC, Heterocyclic Chemistry, 23rd, Glasgow, UK, 2011-07-31–2011-08-04
References
- 1a
E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.). Comprehensive Asymmetric Catalysis, Springer, New York (1999).Google Scholar
- 1b
I. Ojima (Ed.). Catalytic Asymmetric Synthesis, 2nd ed., John Wiley, New York (2000).Google Scholar
- 2a
, A. Pfaltz. Acc. Chem. Res.26, 339 (1993).CrossrefGoogle Scholar
- 2b
, A. K. Ghosh, P. Mathivanan, J. Cappiello. Tetrahedron: Asymmetry9, 1 (1998).CrossrefGoogle Scholar
- 2c
, D. A. Evans, T. Rovis, J. S. Johnson. Pure Appl. Chem.71, 1407 (1999).CrossrefGoogle Scholar
- 2d
, J. S. Johnson, D. A. Evans. Acc. Chem. Res.33, 325 (2000).CrossrefGoogle Scholar
- 2e
, D. Rechavi, M. Lemaire. Chem. Rev.102, 3467 (2002).CrossrefGoogle Scholar
- 2f
, H. A. MacManus, P. J. Guiry. Chem. Rev.104, 4151 (2004).CrossrefGoogle Scholar
- 2g
, G. Desimoni, G. Faita, K. A. Jørgensen. Chem. Rev.106, 3561 (2006).CrossrefGoogle Scholar
- 2h
, G. C. Hargaden, P. J. Guiry. Chem. Rev.109, 2505 (2009).CrossrefGoogle Scholar
- 2i
, P. K. Singh, V. K. Singh. Pure Appl. Chem.82, 1845 (2010).CrossrefGoogle Scholar
- 3
, H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, K. Itoh. Organometallics8, 846 (1989).CrossrefGoogle Scholar
- 4
, For a review on Pybox, see: G. Desimoni, G. Faita, P. Quadrelli. Chem. Rev.103, 3119 (2003).CrossrefGoogle Scholar
- 5
, A. Datta Gupta, D. Bhuniya, V. K. Singh. Tetrahedron50, 13725 (1994).CrossrefGoogle Scholar
- 6a
, A. Datta Gupta, V. K. Singh. Tetrahedron Lett.37, 2633 (1996).CrossrefGoogle Scholar
- 6b
, G. Sekar, A. Datta Gupta, V. K. Singh. J. Org. Chem.63, 2961 (1998).CrossrefGoogle Scholar
- 6c
, S. K. Ginotra, V. K. Singh. Tetrahedron62, 3573 (2006).CrossrefGoogle Scholar
- 6d
, S. K. Ginotra, V. K. Singh. Org. Biomol. Chem.4, 4370 (2006).CrossrefGoogle Scholar
- 7a
, J. Lu, S.-J. Ji, Y.-C. Teo, T.-P. Loh. Org. Lett.7, 159 (2005).CrossrefGoogle Scholar
- 7b
, J. Lu, S.-J. Ji, T.-P. Loh. Chem. Commun. 2345 (2005).CrossrefGoogle Scholar
- 7c
, J. Lu, M.-L. Hong, S.-J. Ji, Y.-C. Teo, T.-P. Loh. Chem. Commun. 4217 (2005).CrossrefGoogle Scholar
- 7d
, J. Lu, S.-J. Ji, Y.-C. Teo, T.-P. Loh. Tetrahedron Lett.46, 7435 (2005).CrossrefGoogle Scholar
- 7e
, W.-Y. Chen, X.-S. Li. Lett. Org. Chem.4, 398 (2007).CrossrefGoogle Scholar
- 8a
, A. Bisai, V. K. Singh. Org. Lett.8, 2405 (2006).CrossrefGoogle Scholar
- 8b
, A. Bisai, V. K. Singh. Tetrahedron68, 3480 (2012).CrossrefGoogle Scholar
- 8c
, M. Panera, J. Diez, I. Merino, E. Rubio, M. P. Gamasa. Inorg. Chem.48, 11147 (2009).CrossrefGoogle Scholar
- 9
, P. K. Singh, V. K. Singh. Org. Lett.10, 4121 (2008).CrossrefGoogle Scholar
- 10
, P. K. Singh, V. K. Singh. Org. Lett.12, 80 (2010).CrossrefGoogle Scholar
- 11
, E. Garribba, G. Micera. J. Chem. Educ.83, 1229 (2006).CrossrefGoogle Scholar
About the article
Published Online: 2012-06-05
Published in Print: 2012-06-05
Citation Information: Pure and Applied Chemistry, Volume 84, Issue 7, Pages 1651–1657, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-11-10-16.
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