Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

高等学校化学研究 ›› 2010, Vol. 26 ›› Issue (1): 50-54.

Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

GAO Jun-long¹, ZHENG Liang-yu², ZHANG Suo-qin^1*, ZHANG Xin-min¹, SUN Guo-dong¹, QIN Lin¹, LI Yao-xian¹, LIU Qing-wen¹ and LI Xiao-bo¹

1. College of Chemistry,
2. Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, Jilin University, Changchun 130021, P. R. China

出版日期:2010-01-04 发布日期:2010-03-29
通讯作者: ZHANG Suo-qin. E-mail: suoqin@jlu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.20802025 and 20082011).

Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

GAO Jun-long¹, ZHENG Liang-yu², ZHANG Suo-qin^1*, ZHANG Xin-min¹, SUN Guo-dong¹, QIN Lin¹, LI Yao-xian¹, LIU Qing-wen¹ and LI Xiao-bo¹

1. College of Chemistry,
2. Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, Jilin University, Changchun 130021, P. R. China

Online:2010-01-04 Published:2010-03-29
Contact: ZHANG Suo-qin. E-mail: suoqin@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20802025 and 20082011).

摘要/Abstract

摘要：

A series of proline-based amino pyridine dipeptide organocatalysts was synthesized and applied in direct asymmetric intermolecular aldol reaction. These catalysts showed good solubility in organic solvents, good yields (73%―97%) and enantioselectivitives(74%―94%). Among them, dipeptide organocatalyst(2) was found to be the most efficient one for the asymmetric aldol reaction between cyclohexanone and 4-nitrobeznaldehyde. After optimi- zing the catalytic reaction conditions, we found that the catalyst showed high yield(97%), enantioselectivity(e.e., up to 92%) and anti-diastereoselectivity(up to 95:5) at mild room temperature without any additives.

关键词: Proline-based dipeptide; Aldol reaction; Enantioselectivity

Abstract:

Key words: Proline-based dipeptide; Aldol reaction; Enantioselectivity

GAO Jun-long, ZHENG Liang-yu, ZHANG Suo-qin*, ZHANG Xin-min, SUN Guo-dong, .... Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction[J]. 高等学校化学研究, 2010, 26(1): 50-54.

参考文献

[1] List B., Lerner R. A., Barbas C. F. III, J. Am. Chem. Soc., 2000, 122, 2395
[2] Dalko P. I., Moisan L., Angew. Chem. Int. Ed., 2001, 40, 3726
[3] Xu Q. Y., Wu T. Q., Pan X. F., Chem. J. Chinese Universities, 2002, 23(7), 1318
[4] List B., Acc. Chem. Res., 2004, 37, 548
[5] Notz W., Tanaka F., Barbas C. F. III, Acc. Chem. Res., 2004, 37, 580
[6] Saito S., Yamamoto H., Acc. Chem. Res., 2004, 37, 570
[7] Liu W. M., Wang P. A., Jiang R., et al., Chem. J. Chinese Universities, 2006, 27(9), 1656
[8] Guillena G., Na'jera C., Ramo'n D. J., Tetrahedron: Asymmetry, 2007, 18, 2249
[9] Mukherjee S., Yang J. W., Hoffmann S., Chem. Rev., 2007, 107, 5471
[10] Saito S., Yamamoto H., Acc. Chem. Res., 2004, 37, 570
[11] Sekiguchi Y., Sasaoka A., Shimomoto A., et al., Synlett., 2003, 1655
[12] Pihko P. M., Laurikainen K. M., Usano A., et al., Tetrahedron, 2006, 62, 317
[13] Hayashi Y., Aratake S., Itoh T., et al., Chem. Commun., 2007, 957
[14] Shen Z. X., Chen W. H., Jiang H., et al., Chirality, 2005, 17, 119
[15] Gruttadauria M., Riela S., Aprile C., et al., Adv. Synth. Catal., 2006, 348, 82
[16] Hartikka A., Arvidsson P. I., Tetrahedron: Asymmetry, 2004, 15, 1831
[17] Torii H., Nakadai M., Ishihara K., et al., Angew Chem. Int. Ed. Engl., 2004, 43, 1983
[18] Berkessel A., Koch B., Lex J., Adv. Synth. Catal., 2004, 346, 1141
[19] Revell J. D., Wennemers H., Tetrahedron, 2007, 63, 8420
[20] Luppi G., Cozzi P. G., Monari M., et al., J. Org. Chem., 2005, 70, 7418
[21] Tang Z., Yang Z. H., Cun L. F., et al., Org. Lett., 2004, 6, 2285
[22] Tang Z., Jiang F., Yu L. T., et al., J. Am. Chem. Soc., 2003, 125, 5262
[23] Tang Z., Yang Z. H., Chen X. H., et al., J. Am. Chem. Soc., 2005, 127, 9285
[24] Nakadai M., Saito S., Yamamoto H., et al., Tetrahedron, 2002, 58, 8167
[25] Chen F. B., Huang S., Zhang H., et al., Tetrahedron, 2008, 64, 9585
[26] Luppi G., Cozzi P. G., Monari M., et al., J. Org. Chem., 2005, 70, 7418
[27] Tang Z., Yang Z. H., Cun L. F., et al., Org. Lett., 2004, 6, 2285
[28] Garcia T. F., Goswami. S., Chang S. K., et al., J. Am. Chem. Soc., 1990, 112, 7393

Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics

本文评价