Neighboring heteroatom effect unique to aqueous aldol reactions of water-insoluble substrates

Journal of Organic Chemistry

Volumn 79, Issue 5, 2014, Pages 2242-2254

  Li, Bo ^a   Li, Chunbao ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL CONDENSATION; ALDOL REACTIONS; AQUEOUS REACTIONS; AROMATIC KETONES; EFFICIENT CATALYSTS; HEMIACETALS; HIGHER YIELD; QUANTITATIVE YIELDS;

CONDENSATION; FUNCTIONAL GROUPS; KETONES; LITHIUM; ORGANIC SOLVENTS;

CONDENSATION REACTIONS;

ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; CARBOHYDRATE; EPOXIDE; ESTER DERIVATIVE; FUNCTIONAL GROUP; KETOL; KETONE DERIVATIVE; LITHIUM; ORGANIC SOLVENT; SILANE DERIVATIVE;

ALDOL REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYST; PURIFICATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME;

EID: 84896770125     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500213b     Document Type: Article

References (44)

1. For comprehensive reviews, see: Modern Aldol reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
2. Cui, X.; Li, B.; Liu, T.; Li, C. Green Chem. 2012, 14, 668-672
3. He, G.; Li, B.; Li, C. J. Agric. Food Chem. 2013, 61, 2913-2918
4. Ikegami, S.; Ohishi, J.; Akaboshi, S. Chem. Pharm. Bull. 1975, 23, 2701-2710
5. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275-3279
6. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302-6337
7. Beattie, J. K.; McErlean, C. S. P.; Phippen, C. B. W. Chem.-Eur. J. 2010, 16, 8972-8974
8. Li, C.-J. Chem. Rev. 2005, 105, 3095-3165
9. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725-748
10. Jung, Y.; Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492-5502
11. Butler, R. N.; Coyne, A. G.; Moloney, E. M. Tetrahedron Lett. 2007, 48, 3501-3503
12. Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173
13. Paquette, L. A.; Wang, T-Z; Vo, N. H. J. Am. Chem. Soc. 1993, 115, 1676-1683
14. Lau, S. Y. W. Org. Lett. 2011, 13, 347-349
15. Hong, B.-C.; Hsu, C.-S.; Lee, G.-H. Chem. Commun. 2012, 48, 2385-2387
16. Davies, J. S.; Higginbotham, C. L.; Tremeer, E. J.; Brown, C.; Treadgold, R. C. J. Chem. Soc., Perkin Trans. 1 1992, 3043-3048
17. You, Y.-J.; Kim, Y.; Nam, N.-H.; Ahn, B.-Z. Bioorg. Med. Chem. Lett. 2003, 13, 3137-3140
18. Djurendić, E. A.; Ajduković, J. J.; Sakač, M. N.; Csanádi, J. J.; Kojić, V. V.; Bogdanović, G. M.; Gaši, K. M. P. Eur. J. Med. Chem. 2012, 54, 784-792
19. Hurst, D. T.; McInnes, A. G. Can. J. Chem. 1965, 43, 2004-2011
20. Menche, D.; Arikan, F.; Li, J.; Rudolph, S. Org. Lett. 2007, 9, 267-270
21. Abed, H. B.; Mammoliti, O.; Bande, O.; Lommen, G. V.; Herdewijn, P. J. Org. Chem. 2013, 78, 7845-7858
22. Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R.; Vila, C. Eur. J. Org. Chem. 2013, 1902-1907
23. Liu, R.; Li, Z.; Zhu, H.; Sun, W. Inorg. Chim. Acta 2012, 387, 383-389
24. Molleti, N.; Rana, N. K.; Singh, V. K. Org. Lett. 2012, 14, 4322-4325
25. Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003-12004
26. Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516
27. Crawford, C.; Nelson, A.; Patel, I. Org. Lett. 2006, 8, 4231-4234
28. Singh, P. K.; Singh, V. K. Org. Lett. 2010, 12, 80-83
29. Dodd, K.; Morton, D.; Worden, S.; Narquizian, R.; Nelson, A. Chem.-Eur. J. 2007, 13, 5857-5861
30. Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003
31. Richard, F.; Carreyre, H.; Coustard, J. M.; Bachmann, C.; Perot, G. Tetrahedron 1998, 54, 14757-14766
32. Casiraghi, G.; Zanardi, F. Chem. Rev. 1995, 95, 1677-1716
33. Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576-1624
34. Reddy, L. V. R.; Kumar, V.; Sagar, R.; Shaw, A. K. Chem. Rev. 2013, 113, 3605-3631
35. Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Nature 2007, 446, 896-899
36. Romeo, G.; Chiacchio, U.; Corsaro, A.; Merino, P. Chem. Rev. 2010, 110, 3337-3370
37. Calvo-Mateo, A.; Camarasa, M.-J.; Diaz-Ortiz, A.; De las Heras, F. G.; Alemany, A. J. Chem. Soc., Pekin Trans. I 1988, 2861-2863
38. Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054-3058
39. Winchester, B. G. Tetrahedron: Asymmetry 2009, 20, 645-651
40. Banday, A. H.; Zargar, M. I.; Ganaie, B. A. Steroids 2011, 76, 1358-1362
41. Dubey, S.; Jindal, D. P.; Piplani, P. Indian J. Chem. B 2005, 44, 2126-2137
42. Huang, L. H.; Zheng, Y. F.; Song, C. J.; Wang, Y. G.; Xie, Z. Y.; Lai, Y. W.; Lu, Y. Z.; Liu, H. M. Steroids 2012, 77, 710-715
43. Stefanović, M.; Miljković, D.; Miljković, M.; Jokić, A.; Stipanovic, B. Tetrahedron Lett. 1966, 7, 3891-3895
44. Dory, I.; Lanyi, G. Acta Chim. Acad. Sci. Hung. 1962, 30, 71-75