Recent Advances in Rh-Catalyzed Asymmetric Hydroformylation of Olefins

doi:10.6023/cjoc201304005

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1369-1381.DOI: 10.6023/cjoc201304005 Previous Articles Next Articles

Reviews

铑催化的烯烃不对称氢甲酰化反应研究进展

贾肖飞^a,b, 王正^b, 夏春谷^a, 丁奎岭^b

a 羰基合成与选择性氧化国家重点实验室中国科学院兰州化学物理研究所兰州 730000;
b 金属有机化学国家重点实验室中国科学院上海有机化学研究所上海 200032

收稿日期:2013-04-06 修回日期:2013-04-22 发布日期:2013-04-24
通讯作者: 丁奎岭 E-mail:kding@mail.sioc.ac.cn
基金资助:
国家自然科学基金(Nos. 21172237, 21121062, 21032009)资助项目.

Recent Advances in Rh-Catalyzed Asymmetric Hydroformylation of Olefins

Jia Xiaofei^a,b, Wang Zheng^b, Xia Chungu^a, Ding Kuiling^b

a State Key Laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2013-04-06 Revised:2013-04-22 Published:2013-04-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172237, 21121062, 21032009).

Hydroformylation is one of the most important processes of homogeneous catalysis in industry. Asymmetric hydroformylation (AHF) of prochiral alkenes provides an efficient way to the synthesis of optically active aldehydes, which are versatile chiral intermediates for pharmaceuticals, agrochemicals, and other fine chemicals. So far, most of methods reported were focused on the use of Rh(I)-based catalysts, by virtue of their high catalytic activity and excellent chemoselectivity for the aldehydes. A key issue in searching for efficient asymmetric hydroformylation catalysts is the development of new chiral ligands. A number of chiral phosphorus ligands have been successfully developed for Rh(I)-catalyzed AHF reactions. In this review, the recent advances in the development of chiral ligands for the Rh-catalyzed asymmetric hydroformylaion of olefins have been surveyed.

Key words: aldehyde, asymmetric catalysis, chiral phosphine ligand, hydroformylation, olefin, rhodium

Cite this article

Jia Xiaofei, Wang Zheng, Xia Chungu, Ding Kuiling. Recent Advances in Rh-Catalyzed Asymmetric Hydroformylation of Olefins[J]. Chin. J. Org. Chem., 2013, 33(07): 1369-1381.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Claver, C.; van Leeuwen, P. W. N. M. Rhodium Catalyzed Hydroformylation, Kluwer Academic Publishers, Dordrecht, 2002. (b) Franke, R.; Selent, D.; Börner, A. Chem. Rev. 2012, 112, 5675. (c) Su, K.; Jiang, H.; Zhu, D.; Fu, H.; Zheng, X.; Yuan, M.; Li, R.; Chen, H. Acta Chim. Sinica, 2013, 71, 844.
[2] Naqvi, S. Oxo Alcohols. Process Economics Program Report 21E, SRI Consulting, Menlo Park, CA, 2010.
[3] (a) Agbossou, F.; Carpentier, J. F.; Mortreaux, A. Chem. Rev. 1995, 95, 2485. (b) Gual, A.; Godard, C.; Castillón, S.; Claver, C. Tetrahedron: Asymmetry 2010, 21, 1135.
[4] Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355.
[5] Botteghi, C.; Consiglio, G.; Pino, P. Chimia 1972, 26, 141.
[6] (a) Ogata, I.; Ikeda, Y. Chem. Lett. 1972, 487. (b) Tanaka, M.; Watanabe, Y.; Mitsudo, T.-A,; Yamamoto, K.; Takeeami, Y. Chem. Lett. 1972, 483.
[7] Salomon, C.; Consiglio, G.; Botteghi, C.; Pino, P. Chimia 1973, 27, 215.
[8] Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183.
[9] (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033. (b) Nozaki, K.; Nanno, T.; Takaya, H. J. Organomet. Chem. 1997, 527, 103. (c) Lambers-Verstappen, M. M. H.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 478.
[10] (a) Saskai, N.; Nozaki, K.; Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 395. (b) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413. (c) Nozaki, K.; Takaya, H.; Hiyama, T. Top. Catal. 1997, 4, 175.
[11] Hoiuchi, T.; Ota, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. J. Org. Chem. 1997, 62, 4285.
[12] Mazuela, J.; Coll, M.; Pàmies, O.; Diéguez, M. J. Org. Chem. 2009, 74, 5440.
[13] Tanaka, R.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72, 8671.
[14] Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772.
[15] (a) Yan, Y.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 7198. (b) Zhang, X.; Cao, B.; Yan, Y.; Yu, S.; Ji, B.; Zhang, X. Chem. Eur. J. 2010, 16, 871.
[16] Zhang, X.; Cao, B.; Yu, S.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047.
[17] Chikkali, S. H.; Bellini, R.; de Bruin, B.; van der Vlugt, J. I.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 6607.
[18] Noonan, G. M.; Fuentes, J. A.; Cobley, C. J.; Clarke, M. L. Angew. Chem., Int. Ed. 2012, 51, 2477.
[19] (a) Babin, J. E.; Whiteker, G. T. US 5360938, 1993 [Chem. Abstr. 1995, 122, 186609]. (b) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
[20] Clark, T. P.; Landis, C. R.; Freed, S. L.; Klosin, J.; Abboud, K. A. J. Am. Chem. Soc. 2005, 127, 5040.
[21] Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillón, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086.
[22] (a) Diéguez, M.; Pàmies, O.; Claver, C. Chem. Commun. 2005, 1221. (b) Gual, A.; Godard, C.; Castillón, S.; Claver, C. Adv. Synth. Catal. 2010, 352, 463.
[23] (a) Cobley, C. J.; Klosin, J.; Qin, C.; Whiteker, G. T. Org. Lett. 2004, 6, 3277. (b) Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.; Whiteker, G. T.; Zanotti-Gerosa, A. J. Org. Chem. 2004, 69, 4031.
[24] Zhao, B.; Peng, X.; Wang, W.; Xia, C.; Ding, K. Chem. Eur. J. 2008, 14, 7847.
[25] Peng, X.; Wang, Z.; Xia, C.; Ding, K. Tetrahedron Lett. 2008, 49, 4862.
[26] Breeden, S.; Cole-Hamilton, D. J.; Foster, D. F.; Schwarz, G. J.; Wills, M. Angew. Chem., Int. Ed. 2000, 39, 4106.
[27] (a) Jiang, Y.; Xue, S.; Li, Z.; Deng, J.; Mi, A.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 3185. (b) Jiang, Y.; Xue, S.; Yu, K.; Li, Z.; Deng, J.; Mi, A.; Chan, A. S. C. J. Organomet. Chem. 1999, 586, 159. (c) Yan, M.; Li, X.-S.; Chan, A. S. C. Chin. J. Chem. 2004, 22, 203.
[28] (a) Klosin, J.; Landis, C. R. Acc. Chem. Res. 2007, 40, 1251. (b) Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng, W.; Rand, C. R.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Org. Lett. 2007, 9, 2665.
[29] McDonald, R. I.; Wong, G. W.; Neupane, R. P.; Stahl, S. S.; Landis, C. R. J. Am. Chem. Soc. 2010, 132, 14027.
[30] Watkins, A. L.; Hashiguchi, B. G.; Landis, C. L. Org. Lett. 2008, 10, 4553.
[31] Clemens, A. J. L.; Burke, S. D. J. Org. Chem. 2012, 77, 2983.
[32] Risi, R. M.; Burke, S. D. Org. Lett. 2012, 14, 1180.
[33] Axtell, A. T.; Cobley, C. J.; Klosin, J.; Whiteker, G. T.; Zanotti-Gerosa, A.; Abboud, K. A. Angew. Chem., Int. Ed. 2005, 44, 5834.
[34] Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223.
[35] Sherill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804.
[36] Tamura, K.; Sugiya, M.; Yoshida, K.; Yanagisawa, K.; Imamoto, T. Org. Lett. 2010, 12, 4400.
[37] (a) Wang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 19080. (b) Uhlemann, M.; Börner, A. ChemCatChem 2012, 4, 753.
[38] (a) Keuelemans, A. I. M.; Kwantes, A.; van Bavel, T. Recl. Trav. Chim. Pays-Bas 1948, 67, 298. (b) Clarke, M. L.; Roff, G. J. Chem.-Eur. J. 2006, 12, 7978.
[39] (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713. (c) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557. (d) Guo, H.; Ding, K.; Dai, L. Chin. Sci. Bull. 2004, 49, 1575 (in Chinese). (郭红超, 丁奎岭, 戴立信, 科学通报, 2004, 49, 1575.) (e) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427. (f) Liu, Y.; Wang, Z.; Ding, K. Acta Chim. Sinica 2012, 70, 1427.
[40] (a) Mazuela, J.; Pàmies, O.; Diéguez, M.; Palais, L.; Rosset, S.; Alexakis, A. Tetrahedron: Asymmetry 2010, 21,2153. (b) Carrilho, R. M. B.; Neves, A. C. B.; Lourenco, M. A. O.; Abreu, A. R.; Rosado, M. T. S.; Abreu, P. E.; Eusébio, M. E. S.; Kollár, L.; Bayón, J. C.; Pereira, M. M. J. Organomet. Chem. 2012, 698, 28. (c) Fan, B.-M.; Xie, J.-H.; Zhou, Z.-T.; Zang, Q.; Tu, Y.-Q.; Zhou, Q.-L. Chem. J. Chin. Univ. 2006, 27, 1984 (in Chinese). (樊保敏, 谢建华, 周章涛, 张齐, 涂永强, 周其林, 高等学校化学学报, 2006, 27, 1984.)
[41] Hua, Z.; Vassar, V. C.; Choi, H.; Ojima, I. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5411.
[42] Li, Y.; Wang, Z.; He, Y.; Fan, Q. Chin. J. Org. Chem. 2010, 30, 338 (in Chinese). (李永，王志玲，何艳梅，范青华，有机化学, 2010, 30, 338.)
[43] Kuil, M.; Goudriaan, P. E.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Commun. 2006, 4679.
[44] Bellini, R.; Reek, J. N. H. Chem. Eur. J. 2012, 18, 13510.
[45] Gadzikwa, T.; Bellini, R.; Dekker, H. L.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 2860.
[46] Breit, B.; Breuninger, D. J. Am. Chem. Soc. 2004, 126, 10244.
[47] Worthy, A. D.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 14757.

铑催化的烯烃不对称氢甲酰化反应研究进展

Recent Advances in Rh-Catalyzed Asymmetric Hydroformylation of Olefins

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[3]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[4]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[5]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[6]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[7]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[8]	Siqiang Fang, Zanjiao Liu, Tianli Wang. Recent Advances of the Atherton-Todd Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1069-1083.
[9]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[10]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[11]	Yuliang Chen, Fengkai He, Siyun Wang, Dingcheng Jia, Yaqun Liu, Yiyong Huang. Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4294-4302.
[12]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[13]	Yan Zeng, Fei Ye. Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3388-3413.
[14]	Xin Kuang, Changhua Ding, Yichen Wu, Peng Wang. Catalytic Enantioselective Preparation of Chiral Allylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3367-3387.
[15]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.