Design, Synthesis and Catalytic Property of L-Proline Derivatives as Organocatalysts for Direct Aldol Reaction
1
조회
0
다운로드
0
인용
0
참고문헌
키워드
초록
A series of chiral prolinamide compounds with pyridine-2, 6-dicarboxylic acid moieties derived from L-proline have been designed and synthesized, their catalytic properties for direct asymmetric aldol reactions were also studied in this article. These catalysts gave the aldol product in high yield (87%) and high enantioselectivity, up to 85%, of the anti-structure at room temperature but gave disappointing results at a lower temperature or when additive was added. Conditions, including solvents, temperature and additives were screened for the reactions. Moreover, the influence of presence of water on yield and stereoselectivity was also discussed.
Abstract
A series of chiral prolinamide compounds with pyridine-2, 6-dicarboxylic acid moieties derived from L-proline have been designed and synthesized, their catalytic properties for direct asymmetric aldol reactions were also studied in this article. These catalysts gave the aldol product in high yield (87%) and high enantioselectivity, up to 85%, of the anti-structure at room temperature but gave disappointing results at a lower temperature or when additive was added. Conditions, including solvents, temperature and additives were screened for the reactions. Moreover, the influence of presence of water on yield and stereoselectivity was also discussed.
참고문헌 (39)
- Hajos, Z. G., , J. Org. Chem, 39, pp.1615~1621 (1974)
- Hajos, Z. G., "Organic Syntheses", pp.363~368 (1990), Wiley
- Hoang, L., , J. Am. Chem. Soc, 125, pp.16~17 (2003)
- Cozzi, P. G., , Eur. J. Org. Chem, pp.5969~5994 (2007)
- Denissova, I., , Tetrahedron, 59, pp.10105~10146 (2003)
- Bella, M., , Synthesis, pp.1583~1614 (2009)
- Rutter, W., , J. Fed. Proc, 23, pp.1248~1257 (1964)
- Barbas, C. F. III., , Angew. Chem, 47(1), pp.42~47 (2008)
- List, B., , J. Am. Chem. Soc, 122, pp.2395~2396 (2000)
- Ramachary, D. B., , Chemistry-A European Journal, 15, pp.4516~4522 (2009)
- Kotsuki, H., , Heterocycles, 75, pp.493~529 (2008)
- Guillena, G., , Tetrahedron: Asymmetry, 18, pp.2249~2293 (2007)
- Northrup, A. B., , Science, 305, pp.1752~1755 (2004)
- Northrup, A. B., , J. Am. Chem. Soc, 124, pp.6798~6799 (2002)
- Dondoni, A., , Angew. Chem, 47, pp.4338~4360 (2008)
- Longbottom, D. A., , Aldrichim. Acta, 41, pp.3~11 (2008)
- Enders, D., , Angew. Chem, 46, pp.1570~1581 (2007)
- Lelias, G., , Aldrichim. Acta, 39, pp.79~87 (2006)
- Houk, K. N., , Eds. Acc. Chem. Res, 37, pp.487~631 (2004)
- Kotsuki, H., , Heterocycles, 75, pp.493~529 (2008)
- Guillena, G., , J. Tetrahedron: Asymmetry, 18, pp.2249~2293 (2007)
- Sakthivel, K., , J. Am. Chem. Soc, 123, pp.5260~5267 (2001)
- Orsini, F., , Tetrahedron, 44, pp.519~541 (1998)
- Hayashi, Y., , Angew. Chem., Int. Ed, 45, pp.958~961 (2006)
- Aratake, S., , Chem. Eur. J, 13, pp.10246~10256 (2007)
- Huang, J., , Angew. Chem., Int. Ed, 46, pp.9073~9077 (2007)
- Tellado, F. G., , J. Am. Chem. Soc, 112, pp.7393~7394 (1990)
- Tang, Z., , Org. Lett, 8, pp.1263~1266 (2006)
- Yang, H., , Carter. Synlett, 19, pp.2827~2838 (2010)
- Yang, H., , J. Org. Chem, 75, pp.72~79 (2010)
- Zhang, Z. G., , Chem. Soc. Rev, 38, pp.1187~1198 (2009)
- Liu, J., , Chirality, 22, pp.432~441 (2010)
- Xacobe, C. C., , Adv. Synth Catal, 1, pp.113~124 (2011)
- Carsten, S., , Chem. Eur. J, 11, pp.1109~1118 (2005)
- Dong, F. S., , Tetrahedron: Asymmetry, 20, pp.2390~2396 (2009)
- Wu, C. L., , Tetrahedron: Asymmetry, 20, pp.1063~1073 (2011)
- Michael, K., , Tetrahedron: Asymmetry, 22, pp.1423~1433 (2011)
- Swapandeep, S. C., , Tetrahedron: Asymmetry, 19, pp.2276~2284 (2008)
- Yang, H., , J. Am. Chem. Soc, 130, pp.9238~9239 (2008)