Enantioselective Analysis: Logic of Chiral Ligand Design for Asymmetric Addition of Diethylzinc to Benzaldehyde

doi:10.6023/cjoc201708066

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 162-170.DOI: 10.6023/cjoc201708066 Previous Articles Next Articles

Special Issue: 庆祝吴养洁院士九十华诞专辑

Articles

对映选择性分析:在二乙基锌与苯甲醛不对称加成中手性配体设计的逻辑推理

王敏灿

郑州大学化学与分子工程学院郑州 450052

收稿日期:2017-08-31 修回日期:2017-09-11 发布日期:2017-10-24
通讯作者: 王敏灿 E-mail:wangmincan@zzu.edu.cn
基金资助:
国家自然科学基金（Nos.21272216，20972140）资助项目.

Enantioselective Analysis: Logic of Chiral Ligand Design for Asymmetric Addition of Diethylzinc to Benzaldehyde

Wang Mincan

College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052

Received:2017-08-31 Revised:2017-09-11 Published:2017-10-24
Contact: 王敏灿 E-mail:wangmincan@zzu.edu.cn
Supported by:
Project supported by the National Natural Sciences Foundation of China (Nos. 21272216, 20972140).

A detailed logic-guided approach towards chiral ligands design is described via the enantioselective analysis of the dynamic conformational behaviors of catalyst, which is based on a mathematical relationship between conformations and enantioselectivity, for asymmetric addition of diethylzinc to benzaldehyde. Following this logic thought, 94 examples, almost all highly enantioselective β-aminoalcohol ligands reported, can be rationally devised by the logic control of the dynamic conformational behaviors of the catalyst from the simplest β-aminoalcohol with one single chiral center as starting point.

Key words: enantioselective analysis, conformational control, rational design, chiral ligand, diethylzinc

Cite this article

Wang Mincan. Enantioselective Analysis: Logic of Chiral Ligand Design for Asymmetric Addition of Diethylzinc to Benzaldehyde[J]. Chin. J. Org. Chem., 2018, 38(1): 162-170.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
[2] (a) Kozlowski, M. C.; Dixon, S. L.; Panda, M.; Lauri, G. J. Am. Chem. Soc. 2003, 125, 6614.
(b) Ianni, J. C.; Annamalai, V.; Phuan, P.-W.; Panda, M.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2006, 45, 5502.
(c) Huang, J.; Ianni, J. C.; Antoline, J. E.; Hsung, R. P.; Kozlowski, M. C. Org. Lett. 2006, 8, 1565.
[3] (a) Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1997, 38, 8773.
(b) Kozlowski, M. C.; Panda, M. J. Org. Chem. 2003, 68, 2061.
[4] (a) Wang, M.-C.; Wang, D.-K.; Zhu, Y.; Liu, L.-T.; Guo, Y.-F. Tetrahedron: Asymmetry 2004, 15, 1289.
(b) Wang, M.-C.; Liu, L.-T.; Zhang, J.-S.; Shi, Y.-Y.; Wang, D.-K. Tetrahedron: Asymmetry 2004, 15, 3853.
(c) Wang, M.-C.; Wang, D.-K.; Lou, J.-P.; Hua, Y.-Z. Chin. J. Chem. 2004, 22, 512.
(d) Wang, M.-C.; Hou, X.-H.; Xu, C.-L.; Liu, L.-T.; Li, G.-L.; Wang, D.-K. Synthesis 2005, 3620.
(e) Xu, C.-L.; Wang, M.-C.; Hou, X.-H.; Liu, H.-M.; Wang, D.-K. Chin. J. Chem. 2005, 23, 155.
(f) Wang, M.-C.; Zhao, W.-X.; Wang, X.-D.; Song, M.-P. Synlett 2006, 3443.
(g) Wang, M.-C.; Hou, X.-H.; Chi, C.-X.; Tang, M.-S. Tetrahedron: Asymmetry 2006, 17, 2126.
(h) Wang, M.-C.; Zhang, Q.-J.; Zhao, W. X.; Wang, X.-D.; Ding, X. J. Org. Chem. 2008, 73, 168.
(i) Wang, M.-C.; Wang, X.-D.; Ding, X.; Liu, Z.-K. Tetrahedron 2008, 64, 2559.
(j) Wang, M.-C.; Zhang, Q.-J.; Li, G.-W.; Liu, Z.-K. Tetrahedron: Asymmetry 2009, 20, 288.
(k) Niu, J.-L.; Wang, M.-C.; Lu, L.-J.; Ding, G.-L.; Lu, H.-J.; Chen, Q.-T.; Song, M.-P. Tetrahedron: Asymmetry 2009, 20, 2616.
(l) Song, X.-X.; Hua, Y.-Z.; Shi, J.-G.; Sun, P.-P.; Wang, M.-C.; Chang, J.-B. J. Org. Chem. 2014, 79, 6087.
(m) Wang, M.-C.; Liu, Z.-K.; Li, S.; Ding, X.; Li, Y.; Tang, M.-S. Tetrahedron: Asymmetry 2010, 21, 486.
(n) Wang, M.-C.; Wang, Y.-H.; Li, G.-W.; Sun, P.-P.; Tie. J.-X.; Lu, H.-J. Tetrahedron: Asymmetry 2011, 22, 761;
(o) Wang, M.-C.; Huang, P.-J.; Yang, X.-C.; Song, X.-X.; Lu, H.-J. Tetrahedron: Asymmetry 2014, 25, 781.
(p) Wang, M.-C.; Li, G.-W.; Hu, W.-B.; Hua, Y.-Z.; Song, X.; Lu, H.-J. Tetrahedron: Asymmetry 2014, 25, 1360.
[5] (a) Seeman, J. I. Chem. Rew. 1983, 83, 83.
(b) Seeman, J. I. J. Chem. Educ. 1986, 63, 42.
[6] Reviews on enantioselective organozinc additions to aldehydes:(a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
(b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
(c) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
(d) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 92.
(e) Walsh, P. Acc. Chem. Res. 2003, 36, 739.
(f) Zhu, H.-J.; Jiang, J.-X.; Ren, J.; Yan, Y.-M.; Pittman, C. U. Curr. Org. Synth. 2005, 2, 547.
(g) Hatano, M.; Miyamoto, T.; Ishihara, K. Curr. Org. Chem. 2007, 11, 127.
[7] (a) M. Yamakawa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 6327.
(b) Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128.
[8] Rasmussen, T.; Norrby, P.-O. J. Am. Chem. Soc. 2003, 125, 5130.
[9] (a) Tsukube, H.; Hosokubo, M.; Wada, M.; Shinoda, S.; Tamiaki, H. J. Chem. Soc., Dalton Trans. 1999, 11.
(b) Tsukube, H.; Hosokubo, M.; Wada, M.; Shinoda, S.; Tamiaki, H. Inorg. Chem. 2001, 40, 740.
[10] Alonso, J. L.; M. Sanz, E.; López, J. C.; Cortijo, V. J. Am. Chem. Soc. 2009, 131, 4320.
[11] (a) Paolucci, C.; Rosini, G. Tetrahedron: Asymmetry 2007, 18, 2923.
(b) Zacharia, J. T.; Tanaka, T.; Uesaka, Y.; Hayashi, M. Sythesis 2012, 44, 1625.
[12] Muchow, G.; Vannoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163.
[13] (a) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690.
(b) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264.
[14] Soai, K.; Konishi, T.; Shibata, T. Heterocycles 1999, 51, 1421.
[15] (a) Bastin, S.; Ginj, M.; Brocard, J.; Pélinski, L.; Novogrocki, G. Tetrahedron: Asymmetry 2003, 14, 1701.
(b) Bastin, S.; Brocard, J.; Pélinski, L. Tetrahedron Lett. 2000, 41, 7303.
[16] (a) Heaton, S. B.; Jones, G. B. Tetrahedron Lett. 1992, 33, 1693.
(b) Jones, G. B.; Heaton, S. B. Tetrahedron: Asymmetry 1993, 4, 261.
[17] Jimeno, C.; Pastó, M.; Riera, A.; Pericàs, M. A. J. Org. Chem. 2003, 68, 3130.
[18] Tseng, S.-L.; Yang, T.-K. Tetrahedron: Asymmetry 2004, 15, 3375.
[19] Nugent, W. A. Org. Lett. 2002, 4, 2133.
[20] Nugent, W. A.; Licini, G.; Bonchio, M.; Bortolini, O.; Finn, M. G.; McClelland, B. W. Pure Appl. Chem. 1998, 70, 1071.
[21] Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970.
[22] Li, S.; Jiang, Y.; Mi, A. Tetrahedron: Asymmetry 1992, 3, 1467.
[23] Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19.
[24] (a) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489.
(b) Cho, B. T.; Chun, Y. S.; Yang, W. K. Tetrahedron: Asymmetry 2000, 11, 2149.
[25] Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M.; Riera, A. J. Org. Chem. 1999, 64, 3969.
[26] Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M.; Riera, A. Synthesis 2000, 1, 165.
[27] Solà, L.; K. Reddy, S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078.
[28] Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691.
[29] (a) Delair, P.; Einhorn, C.; Einhorn, J.; Luche, J. L. J. Org. Chem. 1994, 59, 4680.
(b) Delair, P.; Einhorn, C.; Dinhorn, J.; Luche, J. L. Tetrahedron 1995, 51, 165.
[30] Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529.
[31] Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodriguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123.
[32] Kawanami, Y.; Mitsuie, T.; Miki, M.; Sakamoto, T.; Nishitani, K. Tetrahedron 2000, 56, 175.
[33] Da, C.; Han, Z.; Ni, M.; Yan, F.; Liu, D.; Zhou, Y.; Wang, R. Tetrahedron: Asymmetry 2003, 14, 659.
[34] Yadav, A. K.; Kumar, M.; Yadav, T.; Jain, R. Synlett 2010, 712.
[35] (a) Chrisman, W.; J. Camara, N.; Marcellini, K.; Singaram, B.; Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuk, K. K. Tetrahedron Lett. 2001, 42, 5805.
(b) Steiner, D.; Sethofer, S. G.; Goralski, C. T.; Singaram, B. Tetrahedron: Asymmetry 2002, 13, 1477.
[36] Rachwalski, M. Tetrahedron: Asymmetry 2014, 25, 219.
[37] Kimura, K.; Sugiyama, E.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1992, 33, 3147.
[38] Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832.
[39] Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
[40] Nugent, W. A. J. Chem. Soc., Chem. Commun. 1999, 1369.
[41] Binder, C. M.; Bautista, A.; Zaidlewicz, M.; Krzeminski, M. P.; Oliver, A.; Singaram, B. J. Org. Chem. 2009, 74, 2337.

对映选择性分析:在二乙基锌与苯甲醛不对称加成中手性配体设计的逻辑推理

Enantioselective Analysis: Logic of Chiral Ligand Design for Asymmetric Addition of Diethylzinc to Benzaldehyde

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[2]	Xiang Li, Kai Zhu, Qing Han, Xingxing Lu, Mingjun Li, Yun Ling, Hongxia Duan. Design, Synthesis and Bioactivity Study on Novel Furan α-Butenolactone Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 202-213.
[3]	Li Dai, Di Xu, Yifei Mao, Jiaqi Zhu, Mengjiao Yang. Structures and Synthetic Strategies of Chiral Oxazolinyl Ferrocene Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2364-2375.
[4]	Xu Shuanghua, Chen Jun, Chen Jiarong, Xiao Wenjing. Recent Progress in Applications of Cinchona Alkaloids and Their Derivatives in Asymmetric Catalysis [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3493-3516.
[5]	Li Yao, Luo Sanzhong. Rational Design of Chiral Catalysts Based on Experimental Data and Reaction Mechanism [J]. Chin. J. Org. Chem., 2018, 38(9): 2363-2376.
[6]	Liu Dacai, Zhu Weijun, Zhang Anlin, Yang Nianfa, Yang Liwen. Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes [J]. Chin. J. Org. Chem., 2015, 35(8): 1797-1801.
[7]	Fu Ying, Hou Bo, Zhao Xingling, Du Zhengyin, Hu Yulai. Progress on the Asymmetric Silylcyanation of Aldehydes and Ketones [J]. Chin. J. Org. Chem., 2015, 35(12): 2507-2521.
[8]	Zheng Longsheng, Song Tao, Xu Liwen. 1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp³-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations [J]. Chin. J. Org. Chem., 2014, 34(7): 1255-1267.
[9]	Song Shasha, Zhou Hongyong, Li Xiaona, Wang Lihua, Li Yunqing, Wang Jiaxi. Advance of Glucosamine and Their Derivatives as Chiral Ligands in Asymmetric Syntheses [J]. Chin. J. Org. Chem., 2014, 34(4): 706-716.
[10]	Xue Feng, Li Changgong, Chen Jie, Wan Boshun. Recent Progress of Sulfoxide and N-Sulfinyl Ligands in Asymmetric Catalysis [J]. Chin. J. Org. Chem., 2014, 34(2): 267-277.
[11]	Wang Dong, Hou Chuanjin, Chen Lifeng, Liu Xiaoning, An Qingda, Hu Xiangping. Progress on the Catalytic Asymmetric Hydrogenation of Imines [J]. Chin. J. Org. Chem., 2013, 33(07): 1355-1368.
[12]	Cui Penglei, Liu Huimin, Guo Xiumin, Zhang Dongnuan, Wang Yanen, Wang Chun. Application of Sugar-Based Phosphorus Ligands in Asymmetric Hydrogenation [J]. Chin. J. Org. Chem., 2013, 33(03): 436-443.
[13]	DU Yun-Feng, LI Xin-Sheng, XU Dong-Cheng. Application of Chiral H’4-NOBIN Derivatives in Asymmetric Addition and Alkylation [J]. Chin. J. Org. Chem., 2009, 29(12): 1992-1996.
[14]	Hui, Ailing^a; Zhang, Jintang^b; WANG, Zhiyong^*,b. Progress in Asymmetric Alkyl Addition to Aldehydes and Ketones Promoted by Tartaric Acid Derivatives [J]. Chin. J. Org. Chem., 2009, 29(03): 334-340.
[15]	YANG Wang-Gui^a, WU Shuai^a, SHI Min*^,a,b. Progress of Organozinc Reagents in Asymmetric Addition Reactions Catalyzed by Sulfur-Containing Chiral Ligands [J]. Chin. J. Org. Chem., 2007, 27(02): 197-208.