L-Prolinamide Catalyzed Aqueous Direct Aldol Reaction: an Environment-friendly Method for the Synthesis of β-Hydroxylketones
Yi-Yuan Peng
Key Laboratory of Green Chemistry, Jiangxi Province and Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Key Laboratory of Poyang Lake Ecological Environment and Resource Development, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorHan Liu
Key Laboratory of Green Chemistry, Jiangxi Province and Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorMing Cui
Key Laboratory of Green Chemistry, Jiangxi Province and Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorJin-Pei Cheng
Search for more papers by this authorYi-Yuan Peng
Key Laboratory of Green Chemistry, Jiangxi Province and Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Key Laboratory of Poyang Lake Ecological Environment and Resource Development, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorHan Liu
Key Laboratory of Green Chemistry, Jiangxi Province and Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorMing Cui
Key Laboratory of Green Chemistry, Jiangxi Province and Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorJin-Pei Cheng
Search for more papers by this authorAbstract
An environment-friendly L-prolinamide catalyzed aldol reaction has been developed. The reaction exhibited broad substrate generality,and high yields with good diastereoselectivity were obtained for cyclic ketones. The simplicity of product isolation, usage of water as environmentally benign reaction medium, and the usage of cheap, readily available and recyclable catalyst make this process promising to be developed for large-scale preparation of β-hydroxyl ketones.
REFERENCES
- 1a Anastas, P. T.; Warner, J. C., Green Chemistry, Theory and Practice, Oxford University Press, Oxford, 1998.
- 1b Anastas, P. T.; Williamson, T. C.. Green Chemistry, Frontiers in Benign Chemical Synthesis and Processes, Oxford University Press, Oxford, 1998.
- 1c
Clark, J.;
Macquarrie, D.. Handbook of Green Chemistry and Technology, Blackwell Science, Oxford, 2002.
10.1002/9780470988305 Google Scholar
- 1d Eissen, M.; Metzger, J. O.; Schmidt, E.; Schneidewind, U.. Angew. Chem., Int. Ed., 2002, 41, 414.
- 2a Li, C. J.; Chan, T. H., Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997.
- 2c
Grieco, P. A., Organic Synthesis in Water, Blackie Academic and Professional, London, 1998.
10.1007/978-94-011-4950-1 Google Scholar
- 2d Lindstrom, U. M.. Chem. Rev., 2002, 102, 2751.
- 2e Li, C. J.. Chem. Rev., 2005, 105, 3095.
- 3
Mahrwald, R., Modern Aldol Reactions, Vols. 1–2, Wiley-VCH, Weinheim, 2004.
10.1002/9783527619566 Google Scholar
- 4 List, B.; Lerner, R. A.; Barbas, C. F.III. J. Am. Chem. Soc., 2000, 122, 2395.
- 5For reviews, see:
- 5a
Gröger, H.;
Wilken, J..
Angew. Chem., Int. Ed.,
2001,
40,
529.
10.1002/1521-3773(20010202)40:3<529::AID-ANIE529>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 5b Jarvo, E. R.; Miller, S. J.. Tetrahedron, 2002, 58, 2481.
- 5c List, B.. Tetrahedron, 2002, 58, 5573.
- 5d Duthaler, R. O.. Angew. Chem., Int. Ed., 2003, 42, 975.
- 5e Movassaghi, M.; Jacobsen, E. N.. Science, 2002, 298, 1904.
- 5f Zhong, G. F.. Angew. Chem., Int. Ed., 2003, 42, 4247.
- 6For recently examples of proline and its derivative or analogous compounds catalyzed direct aldol-type reactions, see:
- 6a List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J.. J. Am. Chem. Soc., 2002, 124, 827.
- 6b Córdova, A.; Notz, W.; Zhong, G. F.; Betancort, J. M.; Barbas, C. F. III. J. Am. Chem. Soc., 2002, 124, 1842.
- 6c Córdova, A.; Watanabe, S. I.; Tanaka, F. J.; Notz, W.; Barbas, C. F.III. J. Am. Chem. Soc., 2002, 124, 1866.
- 6d List, B.. J. Am. Chem. Soc., 2002, 124, 5656.
- 6e Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A.. J. Am. Chem. Soc., 2002, 124, 6254.
- 6f Northrup, A. B.; MacMillan, D. W. C.. J. Am. Chem. Soc., 2002, 124, 6798.
- 6g Tang, Z.; Jiang, F.; Yu, L. T.; Cui, X.; Gong, L. Z.; Mi, A. Q.; Jiang, Y. Z.; Wu, Y. D.. J. Am. Chem. Soc., 2003, 125, 5262.
- 6h Halland, N.; Aburel, P. S.; Jørgensen, K. A.. Angew. Chem., Int. Ed., 2003, 42, 661.
- 6i Pidathala, C.; Hoang, L.; Vignola, N.; List, B.. Angew. Chem., Int. Ed., 2003, 42, 2785.
- 6j Fonseca, M. T. H.; List, B.. Angew. Chem., Int. Ed., 2004, 43, 3958.
- 6k Zhang, W.; Saaby, S.; Jørgensen, K. A.. Angew. Chem., Int. Ed., 2004, 43, 4476.
- 6l Enders, D.; Grondal, C.. Angew. Chem., Int. Ed., 2005, 44, 1210.
- 6m Casas, J.; Engqvist, M.; Ibrahem, I.; Kaynak, B.; Córdova, A.. Angew. Chem., Int. Ed., 2005, 44, 1343.
- 6n Wang, W.; Wang, J.; Li, H.. Angew. Chem., Int. Ed., 2005, 44, 1369.
- 6o Sundén, H.; Ibrahem, I.; Eriksson, L.; Córdova, A.. Angew. Chem., Int. Ed., 2005, 44, 4877.
- 6p Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V.. Chem. Commun., 2006, 66.
- 7a Córdova, A.; Notz, W.; Barbas, C. F. III. Chem. Commun., 2002, 3024.
- 7b Peng, Y. Y.; Ding, Q. P.; Li, Z. C.; Wang, P. G.; Cheng, J. P.. Tetrahedron Lett., 2003, 44, 3871.
- 8a Hayashi, Y.; Sumiya, T.; Takahashi, J.. Angew. Chem., Int. Ed., 2006, 45, 958.
- 8b Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F.III. J. Am. Chem. Soc., 2006, 128, 734.
- 9 The yields of the reaction of 1a with 2a in five subsequent runs are 93%, 97%, 96%, 98% and 98%.