Synthetic scope and DFT analysis of the chiral binap-gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes

Beilstein Journal of Organic Chemistry

Volumn 9, Issue , 2013, Pages 2422-2433

  Martín Rodríguez, María ^a   Castelló, Luis M ^a   Nájera, Carmen ^a   Sansano, José M ^a   Larrañaga, Olatz ^b   De Cózar, Abel ^b,c   Cossío, Fernando P ^b  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c BASQUE FOUNDATION FOR SCIENCE   (Spain)

Author keywords

1,3 dipolar cycloaddition; Asymmetric catalysis; DFT; Gold catalysis; NICS; NTR; Oxazolones; Prolines

Indexed keywords

EID: 84888583969     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.9.280     Document Type: Article

References (46)

1. Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584-4671. doi:10.1021/cr050580o (Pubitemid 350225862)
2. Fisk, J. S.; Mosey, R. A.; Tepe, J. J. Chem. Soc. Rev. 2007, 36, 1432-1440. doi:10.1039/b511113g
3. Hewlett, N. M.; Hupp, C. D.; Tepe, J. J. Synthesis 2009, 2825-2839. doi:10.1055/s-0029-1216924
4. Alba, A.-N. R.; Ríos, R. Chem.-Asian J. 2011, 6, 720-734. doi:10.1002/asia.201000636
5. El-Mekabaty, A. Int. J. Mod. Org. Chem. 2013, 2, 40-66.
6. Ávila, E. P.; de Mello, A. C.; Diniz, R.; Amarante, G. W. Eur. J. Org. Chem. 2013, 1881-1883. See for a recent contribution.
7. Uraguchi, D.; Ueki, Y.; Ooi, T. Chem. Sci. 2012, 3, 842-845. doi:10.1039/c1sc00678a See for a recent contribution.
8. Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068-2071. doi:10.1021/ja311363a
9. Zhang, W.-Q.; Cheng, L.-F.; Yu, J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 4085-4088. doi:10.1002/anie.201107741
10. Terada, M.; Tanaka, H.; Sorimachi, K. J. Am. Chem. Soc. 2009, 131, 3430-3431. doi:10.1021/ja8090643
11. Weber, M.; Frey, W.; Peters, R. Adv. Synth. Catal. 2012, 354, 1443-1449. doi:10.1002/adsc.201200085 See for alkylations at multiple positions.
12. Trost, B. M.; Czabaniuk, L. C. J. Am. Chem. Soc. 2012, 134, 5778-5781. doi:10.1021/ja301461p See for alkylations at multiple positions.
13. Dell'Amico, L.; Albrecht, L.; Naicker, T.; Poulsen, P. H.; Jørgensen, K. A. J. Am. Chem. Soc. 2013, 135, 8063-8070. doi:10.1021/ja4029928 See for alkylations at multiple positions.
14. Breman, A. C.; Smits, J. M. M.; de Gelder, R.; van Maarseveen, J. H.; Ingemann, S.; Hiemstra, H. Synlett 2012, 23, 2195-2200. doi:10.1055/s-0032- 1317081 See for participation of a-alkylidene azlactones in 1,3-DC as dipolarophiles.
15. González-Esguevillas, M.; Adrio, J.; Carretero, J. C. Chem. Commun. 2013, 49, 4649-4651. doi:10.1039/c3cc41663a See for participation of a-alkylidene azlactones in 1,3-DC as dipolarophiles.
16. Ho, H. T.; Levere, M. E.; Fournier, D.; Montembault, V.; Pascual, S.; Fontaine, L. Aust. J. Chem. 2012, 65, 970-977. doi:10.1071/CH12192 See for the synthesis of new polymers.
17. Horlacher, O. P.; Hartkoorn, R. C.; Cole, S. T.; Altmann, K.-H. ACS Med. Chem. Lett. 2013, 4, 264-268. doi:10.1021/ml300385q See for the preparation of natural products.
18. Melhado, A. D.; Luparia, M.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12638-12639. doi:10.1021/ja074824t (Pubitemid 350004454)
19. Melhado, A. D.; Amarante, G. W.; Wang, Z. J.; Luparia, M.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 3517-3527. doi:10.1021/ja1095045
20. Hasmi, A. S. K.; Toste, F. D., Eds. Modern Gold Catalyzed Synthesis; Wiley-VCH: Weinheim, Germany, 2012. doi:10.1002/9783527646869
21. Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448-2462. doi:10.1039/c1cs15279c
22. Peixoto de Almeida, M.; Carabineiro, S. A. C. ChemCatChem 2012, 4, 18-29. doi:10.1002/cctc.201100288
23. Bandini, M.; Bottoni, A.; Chiarucci, M.; Cera, G.; Miscione, G. P. J. Am. Chem. Soc. 2012, 134, 20690-20700. doi:10.1021/ja3086774
24. Brazeau, J.-F.; Zhang, S.; Colomer, I.; Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2012, 134, 2742-2749. doi:10.1021/ja210388g And references cited therein.
25. Martín-Rodríguez, M.; Nájera, C.; Sansano, J. M.; Wu, F.-L. Tetrahedron: Asymmetry 2010, 21, 1184-1186. doi:10.1016/j.tetasy.2010. 06.011
26. And see corrigendum Tetrahedron: Asymmetry 2010, 21, 2559-2560.
27. Martín-Rodríguez, M.; Nájera, C.; Sansano, J. M.; de Cózar, A.; Cossío, F. P. Chem.-Eur. J. 2011, 17, 14224-14233. doi:10.1002/chem.201101606
28. Martín-Rodríguez, M.; Nájera, C.; Sansano, J. M.; de Cózar, A.; Cossío, F. P. Beilstein J. Org. Chem. 2011, 7, 988-996. doi:10.3762/bjoc.7.111
29. Martín-Rodríguez, M.; Nájera, C.; Sansano, J. M. Synlett 2012, 62-65. doi:10.1055/s-0030-1260334
30. Wheaton, C. A.; Jennings, M. C.; Puddephatt, R. J. J. Am. Chem. Soc. 2006, 128, 15370-15371. doi:10.1021/ja066450u (Pubitemid 44876002)
31. Wheaton, C. A.; Puddephatt, R. J. Angew. Chem., Int. Ed. 2007, 46, 4461-4463. doi:10.1002/anie.200701325 (Pubitemid 46954594)
32. Wheaton, C. A.; Jennings, M. C.; Puddephatt, R. J. Z. Naturforsch. 2009, 64b, 1569-1577.
33. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378. doi:10.1021/cr068430g See for a comprehensive study of the ligand effects in homogeneous gold(I) catalysis.
34. Satyanarayana, T.; Abraham, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48, 456-494. doi:10.1002/anie.200705241
35. de Cózar, A.; Cossío, F. P. Phys. Chem. Chem. Phys. 2011, 13, 10858-10868. doi:10.1039/c1cp20682f
36. The exo descriptor is referred to the approach of the two reaction components where the tert-butyl ester and carbonyl group of the azlactone are placed in oposite direction.
37. Terada, M.; Nii, H. Chem.-Eur. J. 2011, 17, 1760-1763. doi:10.1002/chem.201003015 The published [4 + 2] cycloaddition of azlactones to β,-unsaturated a-ketoesters was unsuccessfully attempted. Only a low yield of O-alkylation addition product to the ketone group was detected.
38. In ref. [18] and [19] the same result was obtained, but no explanation to this anomalous addition was given.
39. Nájera, C.; de Gracia Retamosa, M.; Sansano, J. M.; de Cózar, A.; Cossío, F. P. Eur. J. Org. Chem. 2007, 5038-5049. doi:10.1002/ejoc.200700267
40. Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 593-609. doi:10.1002/(SICI)1096-987X(19980430)19:6<593::AID-JCC3>3.0.CO; 2-M
41. Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 610-627. doi:10.1002/(SICI)1096-987X(19980430)19:6<610::AID-JCC4>3.0.CO; 2-U
42. Glendening, E. D.; Badenhoop, J. K.; Weinhold, F. J. Comput. Chem. 1998, 19, 628-646. doi:10.1002/(SICI)1096-987X(19980430)19:6<628::AID-JCC5>3.0. CO; 2-T
43. Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Clarendon Press: Oxford, 1900.
44. Lee, M.; Lee, Y.-J.; Park, E.; Park, Y.; Ha, M. W.; Hong, S.; Lee, Y.-J.; Kim, T.-S.; Kim, M.; Park, H. Org. Biomol. Chem. 2013, 11, 2039-2046. doi:10.1039/c3ob27089k See for an example.
45. Kim, Y.; Kim, J.; Park, S. B. Org. Lett. 2009, 11, 17-20. doi:10.1021/ol8022193 See for a regioselective synthesis of tetrasubstituted pyrroles by 1,3-DC from azlactones and spontaneous decarboxylation.
46. Ortiz, A. L.; Echegoyen, L.; Delgado, J. L.; Martin, N. Handb. Carbon Nano Mater. 2011, 1, 325-373. See for retro 1,3-DC, that has also been observed in many thermal processes.