Advancement of Chiral Monodentate Phosphite Ligands in Asymmetric Hydrogenation

doi:10.6023/cjoc202011018

Abstract

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

Cite this article

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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Fig. & Tab. 20

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

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

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

Figure 2. Well-induced mono-phosphonites ligands

Scheme 3. Application of L10c in AH

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

Figure 4. Tropos phosphite ligands

Figure 5. Excellent glycosyl mono-phosphite ligands

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

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

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

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

Figure 10. Excellent Tropos phosphoramidite ligands

Figure 11. Well-induced DpenPhos and CyclamPhos ligands

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

Figure 13. Well-induced chiral spiro phosphoramidite ligands

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

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

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

Figure 16. Methods for recycling catalyst

References 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

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