手性单齿亚磷酸酯配体在不对称氢化反应中的研究进展

doi:10.6023/cjoc202011018

摘要/Abstract

进入21世纪以来, 手性单磷配体特别是手性亚磷酸酯和亚磷酰胺类单磷配体的研究引起了国内外的广泛关注, 这些单齿磷配体的合成简单、原料价格低廉、性质稳定, 同时在不对称催化反应中表现出高活性和对映选择性. 对近二十年来不对称催化氢化领域里手性亚磷酸酯配体的发展历程进行了综述, 介绍了亚膦酸酯(Phosphonites)、亚磷酸酯(Phosphites)和亚磷酰胺(Phosphoramidites)三类单齿磷配体以及由这三类配体衍生出的其他应用.

关键词: 亚磷酸酯, 亚磷酰胺, 亚膦酸酯, 单齿配体, 不对称氢化

Since the 21st century, the study of chiral monophosphorous ligands, especially chiral mono-phosphites ligands and mono-phosphoramidites ligands has attracted widespread attention. This kind of ligands was extensively used in various asymmetric catalytic reactions, for most of them were easily synthesized and showed good stability, high activity and high enantioselectivity. The diverse common monodentate phosphonites, phosphites, and phosphoramidites ligands and their applications in asymmetric hydrogenations over the past two decades are reviewed.

Key words: phosphites, phosphoramidites, phosphonites, monodentate ligands, asymmetric hydrogenation

引用此文

赵芳, 叶文静, 王凯. 手性单齿亚磷酸酯配体在不对称氢化反应中的研究进展[J]. 有机化学, 2021, 41(7): 2650-2665.

Fang Zhao, Wenjing Ye, Kai Wang. Advancement of Chiral Monodentate Phosphite Ligands in Asymmetric Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2650-2665.

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图/表 20

图1. 常见的催化氢化标准底物

Figure 1. Common benchmark substrates for asymmetric hydrogenation (AH)

图式1. 二元混合配体配合物的平衡关系

Scheme 1. Equilibrium relationship between the complexes of binary hybrid ligands

图式2. 反应平衡向二元杂合配体方向进行的方法及其在不对称氢化中的应用

Scheme 2. Method for reaction equilibrium to proceed towards binary hybrid ligand and their application in AH

图2. 诱导效果好的的单齿亚膦酸酯配体

Figure 2. Well-induced mono-phosphonites ligands

图式3. L10c在不对称氢化中的应用

Scheme 3. Application of L10c in AH

图3. BINOL骨架的单齿亚磷酸酯配体及其诱导不对称氢化的底物

Figure 3. A summary of phosphites ligands based on BINOL and their counterpart substrates in AH

图4. Tropos亚磷酸酯配体

Figure 4. Tropos phosphite ligands

图5. 优异的单齿糖基亚磷酸酯配体

Figure 5. Excellent glycosyl mono-phosphite ligands

图6. (a) C3对称的亚磷酸酯配体的顺反异构方式和(b) C3对称的亚磷酸酯配体的螺旋异构方式

Figure 6. (a) Syn- and anti-conformeric forms of C3-symmetric phophites; (b) P and M helical enantiomers of C3-symmetric phosphites

图7. BINOL骨架和H8-BINOL骨架衍生的各类亚磷酰胺配体

Figure 7. Phosphoramidite ligands derived from BINOL and H8-BINOL

图8. Rh/PipPhos催化效果好的底物

Figure 8. Substrates catalysted by Rh/PipPhos with excellent ee

图9. Ir/PipPhos诱导效果好的底物

Figure 9. Substrates with excellent ee induced by Ir/PipPhos

图10. 优异的Tropos亚磷酰胺配体

Figure 10. Excellent Tropos phosphoramidite ligands

图11. 诱导效果好的的DpenPhos和CyclamPhos配体

Figure 11. Well-induced DpenPhos and CyclamPhos ligands

图12. Rh催化的使用DpenPhos诱导效果好的底物

Figure 12. Substrates with excellent ee induced by Rh/ DpenPhos

图13. 诱导效果好的手性螺环亚磷酰胺配体

Figure 13. Well-induced chiral spiro phosphoramidite ligands

图14. Ir催化的使用单齿螺环配体诱导效果好的底物

Figure 14. Substrates with excellent ee induced by chiral spiro iridium phosphoramidite complexes

图15. PhthaPhos、benzaPhos以及由PhthaPhos组装的超分子配合物

Figure 15. PhthaPhos ligand, benzaPhos ligand and the supramolecular complex based on PhthalaPhos

图式4. 通过和PhthaPhos配体形成氢键实现底物的定向定位

Scheme 4. Substrate orientation by forming hydrogen bonding with PhthaPhos ligand

图16. 催化剂回收利用的方法

Figure 16. Methods for recycling catalyst

参考文献 120

[1]	Blaser,H. U.; Schmidt, E. In Asymmetric Catalysis on Industrial Scale, Wiley, New York,2004.
[2]	(a) Chu, W.; Guo, F.; Yu, L.; Hong, J.; Liu, Q.; Mo, F.; Zhang, Y.; Wang, J. Chin. J. Chem. 2018, 36,217. doi: 10.1002/cjoc.v36.3
	(b) Yang, Y.; L., H.; Liu, X.; Liu, T.; Zhu, Y.; Zhang, A.; Mao, G.; Liu, L. Chin. J. Org. Chem. 2019, 39,1655 (in Chinese). doi: 10.6023/cjoc201903050
	( 杨云, 刘慧慧, 刘小兵, 刘田田, 朱玉芹, 张安安, 毛国梁, 刘澜涛, 有机化学, 2019, 39,1655.)
	(c) Xu, R.; Yang, P.; Zheng, C.; You, S. Chin. J. Chem. 2020, 38,683. doi: 10.1002/cjoc.v38.7
	(d) Xing, A.; Tian, M.; Wang, L. Chin. J. Org. Chem. 2016, 36,2912 (in Chinese). doi: 10.6023/cjoc201604022
	( 邢爱萍, 田密, 王来来, 有机化学, 2016, 36,2912.)
	(e) Zhang, F.; Liu, X.; Liu, W.; Deng, G. Chin. J. Org. Chem. 2017, 37,2555 (in Chinese).
	( 张凤, 刘祥华, 刘玮, 邓国军, 有机化学, 2017, 37,2555.)
[3]	Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett,D. J.; Martorell, A.; Orpen,A. G.; Pringle,P. G. Chem. Commun. 2000,961.
[4]	Reetz,M. T.; Mehler, G. Angew. Chem.,Int. Ed. 2000, 39,3889. doi: 10.1002/(ISSN)1521-3773
[5]	van den Berg, M.; Minnaard, A.J.; Schudde, E.P.; vanEsch, J.; de Vries, A.H.M..; de Vries, J.G.; Feringa, B.L. J. Am. Chem. Soc. 2000, 122,11539. doi: 10.1021/ja002507f
[6]	Fu, W.; Tang, W. ACS Catal. 2016, 6,4814. doi: 10.1021/acscatal.6b01001
[7]	(a) Xia, J.; Nie, Y.; Yang, G.; Liu, Y.; Gridnev,I. D.; Zhang, W. Chin. J. Chem. 2018, 36,612. doi: 10.1002/cjoc.v36.7
	(b) Ma, X.; Qiao, L.; Liu, G.; Huang, Z. Chin. J. Chem. 2018, 36,1151. doi: 10.1002/cjoc.v36.12
	(c) Jia, X.; Ren, X.; Wang, Z.; Xia, C.; Ding, K. Chin. J. Org. Chem. 2019, 39,207 (in Chinese).
	( 贾肖飞, 任新意, 王正, 夏春谷, 丁奎岭, 有机化学, 2019, 39,207.)
	(d) Li, S.; Li, Z.; You, C.; Lü, H.; Zhang, X. Chin. J. Org. Chem. 2019, 39,1568 (in Chinese). doi: 10.6023/cjoc201903044
	( 李帅龙, 李庄星, 由才, 吕辉, 张绪穆, 有机化学, 2019, 39,1568.)
	(e) Chen, D.; Xu, M. Chin. J. Org. Chem. 2017, 37,1589 (in Chinese). doi: 10.6023/cjoc201704017
	( 陈雕, 徐明华, 有机化学, 2017, 37,1589.)
	(f) Yu, Y.; Xu, M. Acta Chim. Sinica, 2017, 75,655 (in Chinese). doi: 10.6023/A17040181
	( 于月娜, 徐明华, 化学学报, 2017, 75,655.)
[8]	Rössler,S. L.; Petrone,D. A.; Carreira,E. M. Acc. Chem. Res. 2019, 52,2657. doi: 10.1021/acs.accounts.9b00209
[9]	(a) Knowles,W. S.; Sabacky,M. J. Chem. Commun. (London) 1968, 22,1445.
	(b) Knowles,W. S.; Sabacky,M. J.; Vineyard,B. D. J. Chem. Soc.,Chem. Commun. 1972, 1,10. doi: 10.1038/s42004-018-0009-z
	(c) Vineyard,B. D.; Knowles,W. S.; Sabacky,M. J.; Bachman,G. L.; Weinkauff,D. J. J. Am. Chem. Soc. 1977, 99,5946. doi: 10.1021/ja00460a018
[10]	Knowles,W. S. Acc. Chem. Res. 1983, 16,106. doi: 10.1021/ar00087a006
[11]	Horner, L.; Siegel, H.; Büthe, H. Angew. Chem., nt. Ed. Engl. 1968, 7,942.
[12]	Dang,T. P.; Kagan,H. B. J. Chem. Soc.:Chem. Commun. 1971, 10,481.
[13]	Dang,T. P.; Kagan,H. B. J. Am. Chem. Soc. 1972, 94,6429. doi: 10.1021/ja00773a028
[14]	Reetz,M. T.; Sell, T. Tetrahedron Lett. 2000, 41,6333. doi: 10.1016/S0040-4039(00)01099-6
[15]	Minnaard,A. J.; Feringa,B. L.; Lefort, L.; de Vries,J. G. Acc. Chem. Res. 2007, 40,1267. doi: 10.1021/ar7001107
[16]	Reetz,M. T.; Meiswinkel, A.; Mehler, G.; Angermund, K.; Graf, M.; Thiel, W.; Mynott, R.; Blackmond,D. G. J. Am. Chem. Soc. 2005, 127,10305. doi: 10.1021/ja052025+
[17]	Reetz,M. T.; Sell, T.; Meiswinkel, A.; Mehler, G. Angew. Chem.,Int. Ed. 2003, 42,790. doi: 10.1002/anie.200390209
[18]	Reetz,M. T., Mehler, G. Tetrahedron Lett. 2003, 44,4593. doi: 10.1016/S0040-4039(03)00976-6
[19]	Pena, D.; Minnaard,A. J.; Boogers,J. A.F.; de Vries,A. H.M.; de Vries,J. G.; Feringa,B. L. Org. Biomol. Chem. 2003, 1,1087. doi: 10.1039/b302097e
[20]	Hoen, R.; Boogers,J. A.F.; Bernsmann, H.; Minnaard,A. J.; Meetsma, A.; Tiemersma-Wegman,T. D.; de Vries,A. H.M.; de Vries,J. G.; Feringa,B. L. Angew. Chem., nt. Ed. 2005, 44,4209.
[21]	Reetz,M. T.; Li, X. Chem. Commun. 2006,2159.
[22]	Breit, B.; Seiche, W. J. Am. Chem. Soc. 2003, 125,6608. doi: 10.1021/ja0348997
[23]	Breit, B; Seiche, W. Angew. Chem.,Int. Ed. 2005, 44,1640. doi: 10.1002/(ISSN)1521-3773
[24]	Breit, B. Angew. Chem.,Int. Ed. 2005, 44,6816. doi: 10.1002/(ISSN)1521-3773
[25]	Takacs,J. M.; Reddy,D. S.; Moteki,S. A.; Wu, D.; Palencia, H. J. Am. Chem. Soc. 2004, 126,4494. doi: 10.1021/ja049873+
[26]	(a) Takacs,J. M.; Chaiseeda, K.; Moteki,S. A.; Reddy,D. S.; Chandra, D.; Wu, K. Pure Appl. Chem. 2006, 78,501. doi: 10.1351/pac200678020501
	(b) Moteki,S. A.; Toyama, K.; Liu, Z.; Ma, J.; Holmes,A. E.; Takacs,J. M. Chem. Commun. 2012,263.
[27]	(a) Slagt,V. F.; van Leeuwen,P. W.N. M.; Reek,J. N.H. Chem. Commun. 2003, 19,2474.
	(b) Kuil, M.; Goudriaan,P. E.; van Leeuwen,P. W.N. M.; Reek,J. N.H. Chem Commun, 2006, 45,4679.
	(c) Jiang,X. -B.; van Leeuwen,P. W.N. M.; Reek,J. N.H. Chem. Commun. 2007, 22,2287.
[28]	Frank, D.J; Franzke, A.; Pfaltz, A. Chem.-Eur. J. 2013, 19,2405. doi: 10.1002/chem.v19.7
[29]	Lefort, L.; Boogers,J. A.F.; de Vries,A. H.M.; de Vries,J. G. Org. Lett. 2004, 6,1733. doi: 10.1021/ol049510e
[30]	Lefort, L.; Boogers,J. A.F.; Kuilman, T.; Vijn,R. J.; Janssen, J.; Straatman, H. Org. Process Res. Dev. 2010, 14,568. doi: 10.1021/op100011y
[31]	Alexakis, A.; Rosset, S.; Allamand, J.; March, S.; Guillen, F.; Benhaim, C. Synlett 2001,1375.
[32]	Wunnemann, S.; Frohlich, R.; Hoppe, D. Org. Lett. 2006, 8,2455. doi: 10.1021/ol060528u
[33]	(a) Hu,A. -G.; Fu, Y.; Xie,J. -H.; Zhou, H.; Wang, L.-X; Zhou,Q. -L. Angew. Chem., nt. Ed. 2002, 41,2348.
	(b) Fu, Y.; Guo,X. -X.; Hu,A. -G.; Zhou,Q. -L. J. Org. Chem. 2004, 69,4648. doi: 10.1021/jo049655z
[34]	Fu, Y.; Xie,J. -H.; Hu,A. -G.; Zhou, H.; Wang,L. -X.; Zhou,Q. -L. Chem. Commun. 2002, 5,480.
[35]	Zhu,S. -F.; Fu, Y.; Xie,J. -H.; Liu, B.; Xing, L.; Zhou,Q. -L. Tetrahedron: Asymmetry 2003, 14,3219. doi: 10.1016/j.tetasy.2003.08.017
[36]	Fleming,J. T.; Wills, C.; Waddell,P. G.; Harrington,R. W.; Higham,L. J. Dalton Trans. 2016, 45,15660. doi: 10.1039/C6DT02390H
[37]	Fu, Y.; Hou,G. -H.; Xie,J. -H.; Xing, L.; Wang,L. -X.; Zhou,Q. -L. J. Org. Chem. 2004, 69,8157. doi: 10.1021/jo049146x
[38]	Hou,G. -H.; Xie,J. -H.; Wang,L. -X.; Zhou,Q. -L. J. Am. Chem. Soc. 2006, 128,11774. doi: 10.1021/ja0644778
[39]	Xu,Y. J.; Docherty,G. F.; Woodwardc, G.; Wills, M. Tetrahedron: Asymmetry 2006, 17,2925. doi: 10.1016/j.tetasy.2006.10.036
[40]	van Leeuwen,P. W. N. M.; Kamer,P. C. J.; Claver, C.; Pamies, O.; Dieguez, M. Chem. Rev. 2011, 111,2077. doi: 10.1021/cr1002497
[41]	Diéguez, M.; Pàmies, O.; Claver, C. Tetrahedron: Asymmetry 2004, 15,2113. doi: 10.1016/j.tetasy.2004.04.039
[42]	Alexakis, A.; Bäckvall,J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108,2796. doi: 10.1021/cr0683515
[43]	Reetz,M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43,7941. doi: 10.1016/S0040-4039(02)01838-5
[44]	Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42,2897. doi: 10.1016/S0040-4039(01)00319-7
[45]	Jerphagnon, T.; Renaud,J. L.; Demonchaux, P.; Ferreira, A.; Bruneau, C. Adv. Synth. Catal. 2004, 346,33. doi: 10.1002/(ISSN)1615-4169
[46]	Lyubimov,S. E.; Davankov,V. A.; Loim,N. M.; Popova,L. N.; Petrovskii,P. V.; Valetskii,P. M.; Gavrilov,K. N. J. Organomet. Chem. 2006, 691,5980. doi: 10.1016/j.jorganchem.2006.08.027
[47]	Lynikaite, B.; Cvengros, J.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 2008, 49,755.
[48]	Lyubimov,S. E.; Tyutyunov,A. A.; Kalinin,V. N.; Said-Galiev,E. E.; Khokhlov,A. R.; Petrovskii,P. V. Tetrahedron Lett. 2007, 48,8217. doi: 10.1016/j.tetlet.2007.09.079
[49]	Lyubimov,S. E.; Kalinin,V. N.; Tyutyunov,A. A.; Olshevskaya,V. A.; Dutikova,Y. V.; Safranov,A. S.; Davankov,V. A. Chirality 2009, 21,5.
[50]	Lyubimov,S. E.; Kuchurov,I. V.; Tyutyunov,A. A.; Petrovskii,P. V.; Kalinin,V. N.; Zlotin,S. G.; Davankov,V. A.; Hey-Hawkins, E. Catal. Commun. 2010, 11,419. doi: 10.1016/j.catcom.2009.11.012
[51]	Lyubimov,S. E.; Ozolin,D. V.; Davankov,V. A. Tetrahedron Lett. 2014, 55,3613. doi: 10.1016/j.tetlet.2014.04.113
[52]	Au-Yeung,T. T.-L.; Chan,S. -S.; Chan,A. S.C. Adv. Synth. Catal. 2003, 345,537. doi: 10.1002/adsc.200202192
[53]	Gergely, I.; Hegedüs, C.; Gulyás, H.; Szöllősy, Á.; Monsees, A.; Riermeier, T. Tetrahedron: Asymmetry 2003, 14,1087. doi: 10.1016/S0957-4166(03)00131-9
[54]	Reetz,M. T.; Ma,J. -A.; Goddard, R. Angew. Chem., nt. Ed. 2005, 44,412.
[55]	Dai, Y.; Yang, G.; Zhang, Y.; Zhang, W. Chin. J. Org. Chem. 2008, 28,1169 (in Chinese).
	( 戴轶俊, 杨国强, 张勇健, 张万斌, 有机化学, 2008, 28,1169.)
[56]	Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42,8737. doi: 10.1016/S0040-4039(01)01895-0
[57]	Hannen, P.; Militzer,H. -C.; Vogl,E. M. Chem. Commun. 2003,2210.
[58]	Iuliano, A.; Losi, D.; Facchetti, S. J. Org. Chem. 2007, 72,8472. doi: 10.1021/jo701385y
[59]	Reetz,M. T.; Li, X. Angew. Chem., nt. Ed. 2005,44, :2959.
[60]	Reetz,M. T.; Goossen,L. J.; Meiswinkel, A.; Paetzold, J.; Jensen,J. F. Org. Lett. 2003, 5,3099. doi: 10.1021/ol035076p
[61]	Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. Org. Lett. 2003, 5,4137. doi: 10.1021/ol035551j
[62]	(a) Huang, H.; Liu, X.; Chen, S.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2004, 15,2011. doi: 10.1016/j.tetasy.2004.05.037
	(b) Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. J. Org. Chem. 2004, 69,2355. doi: 10.1021/jo035627p
[63]	(a) Huang, H.; Liu, X.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2005, 16,693. doi: 10.1016/j.tetasy.2004.11.087
	(b) Huang, H.; Liu, X.; Deng, J.; Qiu, M.; Zheng, Z. Org. Lett. 2006, 8,3359. doi: 10.1021/ol0612399
[64]	Alegre, S.; Alberico, E.; Pàmies, O.; Diéguez, M. Tetrahedron: Asymmetry 2014, 25,258. doi: 10.1016/j.tetasy.2013.12.010
[65]	Barakat, A.; Al-Majid,A. M. Arab. J. Chem. 2017, 10,S894. doi: 10.1016/j.arabjc.2012.12.025
[66]	Reetz,M. T.; Guo, H.; Ma,J. -A.; Goddard, R.; Mynott,R. J. J. Am. Chem. Soc. 2009, 131,4136. doi: 10.1021/ja809297a
[67]	Carrilho,R. M.B.; Costa,G. N.; Neves,Â. C.B.; Pereira,M. M.; Grabulosa, A.; Bayón,J. C. Eur. J. Inorg. Chem. 2014, 2014,1034. doi: 10.1002/ejic.v2014.6
[68]	Zhu,S. -F.; Liu, T.; Yang, S.; Song, S.; Zhou,Q. -L. Tetrahedron 2012, 68,7685. doi: 10.1016/j.tet.2012.06.032
[69]	Hu,X. -P.; Wang,D. -S.; Yu,C. -B.; Zhou,Y. -G.; Zheng, Z.; Ma, S., Adventure in Asymmetric Hydrogenation: Synthesis of Chiral Phos- phorus Ligands and Asymmetric Hydrogenation of Heteroaromatics, Springer-Verlag Berlin Heidelberg, 2011, Vol. 36, p. 2557.
[70]	Yuan, Q.; Zhang, W. Chin. J. Org. Chem. 2016, 36,274 (in Chinese). doi: 10.6023/cjoc201509016
	( 袁乾家, 张万斌, 有机化学, 2016, 36,274.)
[71]	Hulst, R.; de Vries,N. K.; Feringa,B. L. Tetrahedron: Asymmetry 1994, 5,699. doi: 10.1016/0957-4166(94)80032-4
[72]	de Veris, A.H.M.; Meetsma, A.; Feringa, B.L. Angew. Chem.,Int. Ed. Engl. 1996, 35,2374. doi: 10.1002/(ISSN)1521-3773
[73]	van den Berg, M.; Minnaard, A.J.; Haak, R.M. Adv. Synth. Catal. 2003, 345,308. doi: 10.1002/adsc.200390026
[74]	Jia, X.; Guo, R.; Li, X. Tetrahedron. Lett. 2002, 43,5541. doi: 10.1016/S0040-4039(02)01142-5
[75]	Peña, D.; Minnaard,A. J.; de Vries,J. G.; Feringa,B. L. J. Am. Chem. Soc. 2002, 124,14552. doi: 10.1021/ja028235t
[76]	Jia, X.; Li, X.; Xu, L. J. Org. Chem. 2003, 68,4539. doi: 10.1021/jo026869c
[77]	Zeng, Q.; Liu, H.; Cui, X. Tetrahedron: Asymmetry 2002, 13,115. doi: 10.1016/S0957-4166(02)00096-4
[78]	Zeng, Q.; Liu, H.; Mi, A. Tetrahedron 2002, 58,8799. doi: 10.1016/S0040-4020(02)01062-1
[79]	Erre, G.; Junge, K.; Enthaler, S.; Addis, D.; Michalik, D.; Spannen- berg, A.; Beller, M. Chem.-Asian J. 2008, 3,887. doi: 10.1002/(ISSN)1861-471X
[80]	Enthaler, S.; Erre, G.; Junge, K.; Schröder, K.; Addis, D.; Michalik, D. Eur. J. Org. Chem. 2008,3352.
[81]	Erre, G.; Enthaler, S.; Junge, K.; Addis, D.; Beller, M. Adv. Synth. Catal. 2009, 351,1437. doi: 10.1002/adsc.v351:9
[82]	Bernsmann, H.; van den Berg, M.; Hoen, R.; Minnaard,A. J.; Mehler, G.; Reetz,M. T. J. Org. Chem. 2005, 70,943. doi: 10.1021/jo048374o
[83]	Panella, L.; Aleixandre,A. M.; Kruidhof,G. J.; Robertus, J.; Feringa,B. L.; de Vries,J. G. J. Org. Chem. 2006, 71,2026. doi: 10.1021/jo052451d
[84]	Panella, L.; Feringa,B. L.; de Vries,J. G. Org. Lett. 2005, 7,4177. doi: 10.1021/ol051559c
[85]	Hekking,K. F.W.; Lefort, L.; de Vries,A. H.M.; van Delft,F. L.; Schoemaker,H. E.; de Vries,J. G. Adv. Synth. Catal. 2008, 350,85. doi: 10.1002/(ISSN)1615-4169
[86]	Feringa,B. L.; de Vries,J. G. Adv. Synth. Catal. 2008, 350,1081. doi: 10.1002/(ISSN)1615-4169
[87]	Feringa,B. L.; de Vries,J. G. Adv. Synth. Catal. 2009, 351,2549. doi: 10.1002/adsc.200900522
[88]	Feringa,B. L.; de Vries,J. G. Tetrahedron: Asymmetry 2010, 21,7. doi: 10.1016/j.tetasy.2009.11.017
[89]	Mršić, N.; Minnaard,A. J.; Feringa,B. L.; Vries,J. G.D. J. Am. Chem. Soc. 2009, 131,8358. doi: 10.1021/ja901961y
[90]	Eberhardt, L.; Armspach, D.; Matt, D.; Toupet, L.; Oswald, B. Eur. J. Org. Chem. 2007, 2007,5395. doi: 10.1002/(ISSN)1099-0690
[91]	Eberhardt, L.; Armspach, D.; Matt, D.; Toupet, L.; Oswald, B. Eur. J. Inorg. Chem. 2007, 26,4153.
[92]	Lyubimov,S. E.; Rastorguev,E. A.; Verbitskaya,T. A.; Petrovskii,P. V.; Hey-Hawkins, E.; Kalinin,V. N.; Davankov,V. A. Polyhedron 2011, 30,1258. doi: 10.1016/j.poly.2011.02.003
[93]	Schmitz, C.; Leitner, W.; Franciò, G. Eur. J. Org. Chem. 2015,2889.
[94]	Renom-Carrasco, M.; Gajewski, P.; Pignataro, L.; de Vries,J. G.; Piarulli, U.; Gennari, C. Adv. Synth. Catal. 2016, 358,2589. doi: 10.1002/adsc.v358.16
[95]	Eberhardt, L.; Armspach, D.; Harrowfield, J.; Matt, D. Chem. Soc. Rev. 2008, 37,839. doi: 10.1039/b714519e
[96]	Monti, C.; Gennari, C.; Piarulli, U.; de Vries,J. G.; de Vries,A. H.M.; Lefort, L. Chem.-Eur. J. 2005, 11,6701. doi: 10.1002/(ISSN)1521-3765
[97]	97 Giacomina, F.; Meetsma, A.; Panella, L.; Lefort, L.; de Vries, A. H. M.; de Vries, J. G. Angew. Chem.,Int. Ed. 2007, 46,1497.
[98]	(a) Liu, Y.; Ding, K. J. Am. Chem. Soc. 2005, 127,10488. doi: 10.1021/ja052749l
	(b) Liu, Y.; Sandoval,C. A.; Yamaguchi, Y.; Zhang, X.; Wang, Z.; Kato, K.; Ding, K. J. Am. Chem. Soc. 2006, 128,14212. doi: 10.1021/ja063350f
	(c) Zhang,J. Z.; Li, Y.; Wang, Z.; Ding, K. Angew. Chem.,Int. Ed. 2011, 50,11743. doi: 10.1002/anie.201104912
	(d) Zhang,J. Z.; Dong, K.; Wang, Z.; Ding, K. Org. Biomol. Chem. 2011, 11,1598. doi: 10.1039/c3ob27345h
	(e) Liu, Y.; Wang, Z.; Ding, K. Acta Chim. Sinica 2012, 70,1464 (in Chinese). doi: 10.6023/A12030050
	( 刘龑, 王正, 丁奎岭, 化学学报, 2012, 70,1464.)
[99]	Zhao, B.; Wang, Z.; Ding, K. Adv. Synth. Catal. 2006, 348,1049. doi: 10.1002/(ISSN)1615-4169
[100]	Liu, Y.; Wang, Z.; Ding, K. Tetrahedron 2012, 68,7581. doi: 10.1016/j.tet.2012.05.096
[101]	Zhang, J.; Dong, K.; Wang, Z.; Ding, K. Org. Biomol. Chem. 2012, 10,1598. doi: 10.1039/c1ob06835k
[102]	Hou,G. -H.; Xie,J. -H.; Yan,P. -C.; Zhou,Q. -L. J. Am. Chem. Soc. 2009, 131,1366. doi: 10.1021/ja808358r
[103]	Yan,P. -C.; Xie,J. -H.; Hou,G. -H.; Wang,L. -X.; Zhou,Q. -L. Adv. Synth. Catal. 2009, 351,3243. doi: 10.1002/adsc.v351:18
[104]	Xie,J. -H.; Yan,P. -C.; Zhang,Q. -Q.; Yuan,K. -X.; Zhou,Q. -L. ACS Catal. 2012, 2,561. doi: 10.1021/cs300069g
[105]	Schmitz, C.; Leitner, W.; Franciò, G. Eur. J. Org. Chem. 2015,6205.
[106]	Hattori, G.; Hori, T.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2007, 129,12930. doi: 10.1021/ja075231l
[107]	Li, Y.; Feng, Y.; He,Y. M.; Chen, F.; Pan, J.; Fan,Q. -H. Tetrahedron Lett. 2008, 49,2878.
[108]	Pignataro, L.; Lynikaite, B.; Cvengros, J.; Marchini, M.; Piarulli, U.; Gennari, C. Eur. J. Org. Chem. 2009, 2009,2539. doi: 10.1002/ejoc.v2009:15
[109]	Pignataro, L.; Carboni, S.; Civera, M.; Colombo, R.; Piarulli, U.; Gennari, C. Angew. Chem.,Int. Ed. 2010, 49,6633. doi: 10.1002/anie.201002958
[110]	Pignataro, L.; Boghi, M.; Civera, M.; Carboni, S.; Piarulli, U.; Gennari, C. Chem.-Eur. J. 2012, 18,1383. doi: 10.1002/chem.v18.5
[111]	Pignataro, L.; Bovio, C.; Civera, M.; Piarulli, U.; Gennari, C. Chem.-Eur. J. 2012, 18,10368. doi: 10.1002/chem.201201032
[112]	Li, Y.; He,Y. -M.; Li,Z. -W.; Zhang, F.; Fan,Q. -H. Org. Biomol. Chem. 2009, 7,1890. doi: 10.1039/b823047a
[113]	Wieland, J; Breit, B. Nat. Chem. 2010, 2,832. doi: 10.1038/nchem.800
[114]	Doherty, S.; Robins,E. G.; Pál, I.; Newman,C. R.; Hardacre, C.; Rooney, D. Tetrahedron: Asymmetry 2003, 14,1517. doi: 10.1016/S0957-4166(03)00253-2
[115]	Simons, C.; Hanefeld, U.; Arends,I. W. C. E.; Minnaard,A. J.; Maschmeyer, T.; Sheldon,R. A. Chem. Commun. 2004,2830.
[116]	Wang,X. W.; Ding,K. L. J. Am. Chem. Soc. 2004, 126,10524. doi: 10.1021/ja047372i
[117]	Hu,X. -P.; Huang,J. -D.; Zeng,Q. -H.; Zheng, Z. Chem. Commun. 2006,293.
[118]	Zhao, Y.; Huang, H.; Shao, J.; Xia, C. Tetrahedron: Asymmetry 2011, 22,769. doi: 10.1016/j.tetasy.2011.04.011
[119]	Escárcega-Bobadilla,M. V.; Rodríguez-Pérez, L.; Teuma, E. Catal. Lett. 2011, 141,808. doi: 10.1007/s10562-011-0568-4
[120]	Zhang, X.; Liu, X.; Peng, J.; Zhao, Y.; Yang, Q. Catal. Sci. Technol. 2014, 4,1012. doi: 10.1039/C3CY01063E