Diastereo- and enantioselective catalytic vinylogous mukaiyama-mannich reactions of pyrrole-based silyl dienolates with alkyl-substituted aldehydes

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 10291-10298

  Ranieri, Beatrice ^a   Curti, Claudio ^a   Battistini, Lucia ^a   Sartori, Andrea ^a   Pinna, Luigi ^b   Casiraghi, Giovanni ^a   Zanardi, Franca ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-SELECTIVITY; CHIRAL LIGAND; CHIRALITY TRANSFER; ENANTIOSELECTIVE; HIGH YIELD; NATURALLY OCCURRING; REACTION COURSE;

ALDEHYDES; AMINO ACIDS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

CATALYST SELECTIVITY;

ALDEHYDE; CARBONYL DERIVATIVE; ISOVALERALDEHYDE; LACTAM DERIVATIVE; LIGAND; PYRROLE DERIVATIVE; SILANE DERIVATIVE; SILVER; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHIRALITY; DIHYDROXYLATION; ENANTIOMER; ENANTIOSELECTIVITY; MANNICH REACTION; MUKAIYAMA REACTION; REACTION TIME; STEREOCHEMISTRY;

ALDEHYDES; AMINO ACIDS; AZA COMPOUNDS; BIOLOGICAL AGENTS; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; IMINES; LACTONES; MOLECULAR STRUCTURE; PYRROLES; SILVER; STEREOISOMERISM;

EID: 84055217181     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201875a     Document Type: Article

References (36)

1. see: (a) Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161.
2. (b) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
3. (c) Viso, A.; de la Pradilla, R. F.; García, A.; Flores, A. Chem. Rev. 2005, 105, 3167.
4. (d) Saibabu Kotti, S. R. S; Timmons, C.; Li, G. Chem. Biol. Drug Des. 2006, 67, 101.
5. (a) Zhong, Y.-W.; Izumi, K.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2004, 6, 4747.
6. (b) Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 5073.
7. (a) Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
8. (b) Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgensen, K. A. J. Am. Chem. Soc. 2001, 123, 5843.
9. (c) Rondot, C.; Zhu, J. Org. Lett. 2005, 7, 1641.
10. (d) Chowdari, N. S.; Ahmad, M.; Albertshofer, K.; Tanaka, F.; Barbas, C. F. III. Org. Lett. 2006, 8, 2839.
11. see: (a) Bernardi, L.; Gothelf, A. S.; Hazell, R G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583.
12. (b) Ooi, T.; Kameda, M.; Fuji, J.; Maruoka, K. Org. Lett. 2004, 6, 2397.
13. (c) Hernandez-Toribio, J.; Arrayas, R G.; Carretero, J. C. J. Am. Chem. Soc. 2008, 130, 16150.
14. (d) Shang, D.; Liu, Y. L.; Zhou, X.; Liu, X.; Feng, X. Chem.-Eur. J. 2009, 15, 3678.
15. (e) Liang, G; Tong, M.-C.; Tao, H.; Wang, C.-J. Adv. Synth. Catal. 2010, 352, 1851.
16. see: (a) Casiraghi, G; Zanardi, F.; Appendino, G; Rassu, G Chem. Rev. 2000, 100, 1929.
17. (b) Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221.
18. (c) Martin, S. F. Acc. Chem. Res. 2002, 35, 895.
19. (d) Casiraghi, G; Zanardi, F.; Battistini, L.; Rassu, G Synlett 2009, 1525.
20. (e) Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G; Zanardi, F. Chem. Rev 2011, 111, 3076.
21. (f) Dudot, B.; Chiaroni, A.; Royer, J. Tetrahedron Lett. 2000, 41, 6355.
22. (g) DeGoey, D. A.; Chen, H.-J.; Flosi, W. J.; Grampovnik, D. J.; Yeung, C. M.; Klein, L. L.; Kempf, D. J. J. Org. Chem. 2002, 67, 5445.
23. (h) Yang, Y.; Phillips, D. P.; Pan, S. Tetrahedron Lett. 2011, 52, 1549.
24. (i) Ruan, S.-T.; Luo, J.-M.; Du, Y.; Huang, P.-Q. Org. Lett. 2011, 13, 4938.
25. Curti, C.; Battistini, L.; Ranieri, B.; Pelosi, G.; Rassu, G; Casiraghi, G; Zanardi, F. J. Org. Chem. 2011, 76, 2248.
26. (a) Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230.
27. (b) Mandai, H.; Mandai, K.; Snapper, M. L.; Hoveyda, A H. J. Am. Chem. Soc. 2008, 130, 17961.
28. (c) Wieland, L. C.; Vieira, E. M.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 570.
29. Curti, C.; Ranieri, B.; Battistini, L.; Rassu, G; Zambrano, V.; Pelosi, G; Casiraghi, G; Zanardi, F. Adv. Synth. Catal. 2010, 352, 2011.
30. See: Sartori, A.; DellAmico, L.; Curti, C.; Battistini, L.; Pelosi, G; Rassu, G; Casiraghi, G; Zanardi, F. Adv. Synth. Catal. 2011, in press.
31. see: (a) Bunch, L.; Norrby, P.-O.; Frydenvang, K.; Krogsgaard-Larsen, P.; Madsen, U. Org. Lett. 2001, 3, 433.
32. (b) Quijada, F. J.; Gotor, V; Rebolledo, F. Org. Lett. 2010, 12, 3602.
33. (a) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807.
34. (b) Gawroński, J.; Gawrońska, K.; Kwit, M.; Kacprzak, K.; Rychlewska, U. Chirality 2004, 16, 405.
35. (c) Cuiper, A. D.; Brzostowska, M.; Gawroński, J. K.; Smeets, W. J. J.; Spek, A. L.; Hiemstra, H.; Kellogg, R. M.; Feringa, B. L. J. Org. Chem. 1999, 64, 2567.
36. Prasad, K. R.; Gholap, S. L. J. Org. Chem. 2008, 73, 2.