Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds

Tetrahedron Letters

Volumn 53, Issue 15, 2012, Pages 1958-1960

  Verrier, Cécile ^a,b   Oudeyer, Sylvain ^a   Dez, Isabelle ^b   Levacher, Vincent ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

Carbonyl compounds; Lewis bases; Nucleophilic addition; Organocatalysis; Renewable resources

Indexed keywords

ALGINIC ACID; AMMONIA; AMMONIUM ALGINATE; CALCIUM ALGINATE; CARBONYL DERIVATIVE; LEWIS BASE; NUCLEOPHILE; UNCLASSIFIED DRUG;

ARTICLE; BROWN ALGA; CARBOHYDRATE ANALYSIS; CATALYST; CELL WALL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

PHAEOPHYCEAE;

EID: 84858161642     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.012     Document Type: Article

References (21)

1. A. Berkessel, and H. Gröger Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis 2005 Wiley-VCH GmbH & Co. KGaA Weinheim
2. J. Baudoux, K. Perrigaud, P.-J. Madec, A.-C. Gaumont, and I. Dez Green Chem. 9 2007 1346 1351
3. E. Guibal Prog. Polym. Sci. 30 2005 71 109
4. D.J. Macquarrie, and J.J.E. Hardy Ind. Eng. Chem. Res. 44 2005 8499 8520
5. A. Ricci, L. Bernardi, C. Gioia, S. Vierucci, M. Robitzer, and F. Quignard Chem. Commun. 46 2010 6288 6290
6. K.R. Reddy, K. Rajgopal, C.U. Maheswari, and M. Lakshmi Kantam New J. Chem. 30 2006 1549 1552
7. Y. Cui, H. Zhang, R. Li, Y. Liu, and C. Xu Chin. J. Org. Chem. 30 2010 707 712
8. T. Pathak, J. Kim, S.-J. Lee, D.-J. Baek, and K.-J. Paeng J. Polym. Environ. 16 2008 198 204
9. N.O. Dhoot, and M.A. Wheatley J. Pharm. Sci. 92 2003 679 689
10. K. Rajender Reddy, K. Rajgopal, and M. Lakshmi Kantam Catal. Lett. 114 2007 36 40
11. F. Quignard, R. Valentin, and F. Di Renzo New J. Chem. 32 2008 1300 1310
12. C. Jouannin, I. Dez, A.C. Gaumont, J.M. Taulemesse, T. Vincent, and E. Guibal Appl. Catal., B 103 2011 444 452
13. Y. Kawano, N. Kaneko, and T. Mukaiyama Chem. Lett. 34 2005 1508 1509
14. For selected examples of 1,2-addition of alkylnitriles, see and references therein: S. Matsukawa, and E. Kitazaki Tetrahedron Lett. 49 2008 2982 2984
15. T. Poisson, V. Gembus, S. Oudeyer, F. Marsais, and V. Levacher J. Org. Chem. 74 2009 3516 3519
16. K. Wadhwa, and J.G. Verkade J. Org. Chem. 74 2009 5683 5686
17. S.R. Jameela, and A. Jayakrishnan Biomaterials 16 1995 769 775
18. T. Hashimoto, and K. Maruoka Chem. Rev. 107 2007 5656 5682
19. Y. Arakawa, N. Haraguchi, and S. Itsuno Angew. Chem., Int. Ed. 47 2008 8232 8235
20. T. Tozawa, H. Nagao, Y. Yamane, and T. Mukaiyama Chem. Asian J. 2 2007 123 134
21. N. Zhu, B.-C. Ma, Y. Zhang, and W. Wang Adv. Synth. Catal. 352 2010 1291 1295