Progress on Transition Metal-Catalyzed Asymmetric Allylic Alkylation Reaction of 1, 3-Dicarbonyl Compounds
- Corresponding author: Song Wangze, wzsong@dlut.edu.cn
Citation:
Zheng Nan, Song Wangze. Progress on Transition Metal-Catalyzed Asymmetric Allylic Alkylation Reaction of 1, 3-Dicarbonyl Compounds[J]. Chinese Journal of Organic Chemistry,
;2017, 37(5): 1099-1110.
doi:
10.6023/cjoc201702013
Bonne, D.; Coquerel, Y.; Constaniteux, T.; Rodriguez, J. Tetrahedron: Asymmetry 2010, 21, 1085.
doi: 10.1016/j.tetasy.2010.04.045
Schotes, C.; Mezzetti, A. ACS Catal. 2012, 2, 528.
doi: 10.1021/cs300035m
Govender, T.; Arvidsson, P. I.; Maguire, G. E. M.; Kruger, H. G.; Naicker, T. Chem. Rev. 2016, 116, 9375.
doi: 10.1021/acs.chemrev.6b00156
Yan, Z.; Jin, H.; Yu, X.; Wang, W.; Tian, W. Chin. J. Org. Chem. 2017, 37, 196 (in Chinese).
Chang, L.; Lai, J.; Yuan, G. Chin. J. Chem. 2016, 34, 887.
doi: 10.1002/cjoc.201600255
Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
doi: 10.1002/(ISSN)1521-3773
Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11943.
doi: 10.1073/pnas.0402416101
Trost, B. M.; Jiang, C. Synthesis 2006, 369.
Das, J. P.; Chechik, H.; Marek, I. Nat. Chem. 2009, 1, 128.
doi: 10.1038/nchem.131
Frost, C. G.; Howart, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
doi: 10.1016/S0957-4166(00)82091-1
Moberg, C.; Bremberg, U.; Hallman, K.; Svensson, M.; Norrby, P.-O.; Hallberg, A.; Larhed, M.; Csoregh, I. Pure Appl. Chem. 1999, 71, 1477.
Tsuji, J. Pure Appl. Chem. 1999, 71, 1539.
Tsuji, J. New J. Chem. 2000, 24, 127.
doi: 10.1039/a909473c
You, S-L.; Zhu, X-Z.; Hou X-L.; Dai, L-X. Acta. Chim. Sinica 2001, 59, 1667 (in Chinese).
doi: 10.3321/j.issn:0251-0790.2001.10.009
Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.
doi: 10.1248/cpb.50.1
Graening, T.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2003, 42, 2580.
doi: 10.1002/anie.200301644
Wang, Q.; Gao, Y.; Meng, X.; Li, X.; Xu, D. Chin. J. Org. Chem. 2009, 29, 776 (in Chinese).
Cui, P.; Liu, H.; Zhang, D.; Wang, C. Chin. J. Org. Chem. 2012, 32, 1401 (in Chinese).
Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387.
doi: 10.1016/S0040-4039(00)71674-1
Tsuji, J. Acc. Chem. Res. 1969, 2, 144.
doi: 10.1021/ar50017a003
Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 11, 3821.
doi: 10.1016/S0040-4039(01)98599-5
Hata, G.; Takahashi, K.; Miyake, A. J. Chem. Soc., Chem. Commun. 1970, 1392.
Trost, B. M.; Fullerton, T. J. J. Am. Chem. Soc. 1973, 95, 292.
doi: 10.1021/ja00782a080
Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649.
doi: 10.1021/ja00447a064
Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
doi: 10.1021/cr9409804
Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
doi: 10.1021/cr020027w
Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258.
doi: 10.1002/(ISSN)1521-3773
Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. 1997, 36, 2108.
doi: 10.1002/(ISSN)1521-3773
Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227.
doi: 10.1021/jo991615l
Fiaud, J. C.; De Gournay, A. H.; Larcheveque, M.; Kagan, H. B. J. Organomet. Chem. 1978, 154, 175.
doi: 10.1016/S0022-328X(00)83439-7
Hayashi, T.; Kanehira, K.; Tsuchiya, H.; Kumada, M. J. Chem. Soc., Chem. Commun. 1982, 1162.
Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
doi: 10.1021/jo00236a023
Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 2586.
doi: 10.1021/ja00033a035
Faller, J. W.; Chao K.-H. J. Am. Chem. Soc. 1983, 105, 3893.
doi: 10.1021/ja00350a026
Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161.
doi: 10.1016/0022-328X(90)85129-M
Faller, J. W.; Mazzieri, M. R.; Nguyen, J. T.; Parr, J.; Tokunaga, M. Pure Appl. Chem. 1994, 66, 1463.
Lloyd, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. 1995, 34, 462.
doi: 10.1002/(ISSN)1521-3773
Trost, B. M.; Dogra, K.; Hachiya, I.; Emura, T.; Hughes, D. L.; Krska, S.; Reamer, R. A.; Palucki, M.; Yasuda, N.; Reider, P. J. Angew. Chem., Int. Ed. 1995, 34, 462.
doi: 10.1002/(ISSN)1521-3773
Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
doi: 10.1021/ja973298a
Glorius, F.; Pfaltz, A. Org. Lett. 1999, 1, 141.
doi: 10.1021/ol990602r
Kaiser, N.-F. K.; Bremberg, U.; Larhed, M.; Moberg, C.; Hallberg, A. Angew. Chem., Int. Ed. 2000, 39, 3595.
doi: 10.1002/(ISSN)1521-3773
Malkov, A. V.; Spoor, P.; Vinader, V.; Kocovsky, P. Tetrahedron Lett. 2001, 42, 509.
doi: 10.1016/S0040-4039(00)02007-4
Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
doi: 10.1016/S0040-4039(97)10220-9
Bartels, B.; Helmchen, G. Chem. Commun. 1999, 35, 741.
Bartels, B.; Garcia-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2002, 2569.
doi: 10.1002/1099-0682(200210)2002:10<2569::AID-EJIC2569>3.0.CO;2-5
Lipowsky, G.; Miller, N.; Helmchen, G. Angew. Chem., Int. Ed. 2004, 43, 4595.
doi: 10.1002/(ISSN)1521-3773
García-Yebra, C.; Janssen, J. P.; Rominger, F.; Helmchen, G. Organometallics 2004, 23, 5459.
doi: 10.1021/om0401105
Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 43, 675.
Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997, 119, 7879.
doi: 10.1021/ja971523i
Trost, B. M.; Schroeder, G. M.; Kristensen, J. Angew. Chem., Int. Ed. 2002, 41, 3492.
doi: 10.1002/1521-3773(20020916)41:18<3492::AID-ANIE3492>3.0.CO;2-P
Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236.
doi: 10.1021/ja9900104
Kuwano, R.; Ito, Y. Org. Lett. 1999, 1, 837.
doi: 10.1021/ol990679f
Brunel, J. M.; Tenaglia, A.; Buono, G. Tetrahedron: Asymmetry 2000, 11, 3585.
doi: 10.1016/S0957-4166(00)00337-2
Kuwano, R.; Uchida, K.; Ito, Y. Org. Lett. 2003, 5, 2177.
doi: 10.1021/ol034665s
Hayashi, T.; Okada, A.; Suzuka, T.; Kawatsura, M. Org. Lett. 2003, 5, 1713.
doi: 10.1021/ol0343562
Selvakumar, K.; Valentini, M.; Pregosin, P. S. Organometallics 1999, 18, 4591.
doi: 10.1021/om990452o
Liu, W.-B.; Reeves, C. M.; Virgil, S. C.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 10626.
doi: 10.1021/ja4052075
Liu, W.-B.; Reeves, C. M.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 17298.
doi: 10.1021/ja4097829
Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
doi: 10.1021/acscatal.6b01886
Trost, B. M.; Donckele, E. J.; Thaisrivongs, D. A.; Osipov, M.; Masters, J. T. J. Am. Chem. Soc. 2015, 137, 2776.
doi: 10.1021/jacs.5b00786
Liu, W-B.; Okamoto, N.; Alexy, E. J.; Hong, A. Y.; Tran, K.; Stoltz, B. M. J. Am. Chem. Soc. 2016, 138, 5234.
doi: 10.1021/jacs.6b02153
Frölander, A.; Lutsenko, S.; Privalov, T.; Moberg, C. J. Org. Chem. 2005, 70, 9882.
doi: 10.1021/jo051610q
Bellini, R.; Magre, M.; Biosca, M.; Norrby, P.-O.; Pàmies, O.; Diéguez, M.; Moberg, C. ACS Catal. 2016, 6, 1701.
doi: 10.1021/acscatal.5b02766
Wang, Q.-F.; He, W.; Liu, X.-Y.; Chen, H.; Qin, X.-Y.; Zhang, S.-Y. Tetrahedron: Asymmetry 2008, 19, 2447.
doi: 10.1016/j.tetasy.2008.10.030
Noël, T.; Bert, K.; Van der Eycken, E.; Van der Eycken, J. Eur. J. Org. Chem. 2010, 2010, 4056.
doi: 10.1002/ejoc.201000238
Cheng, H.-G.; Feng, B.; Chen, L.-Y.; Guo, W.; Yu, X.-Y.; Lu, L.-Q.; Chen. J.-R.; Xiao, W.-J. Chem. Commun. 2014, 50, 2973.
doi: 10.1039/c4cc90058h
Magre, M.; Biosca, M.; Norrby, P.-O.; Pàmies, O.; Diéguez, M. ChemCatChem 2015, 7, 4091.
doi: 10.1002/cctc.201500873
Xu, J.-X.; Ye, F.; Bai, X.-F.; Zhang, J.; Xu, Z.; Zheng, Z.-J.; Xu, L.-W. RSC Adv. 2016, 6, 45495.
doi: 10.1039/C6RA09657C
Liu, Q.-L.; Chen, W.; Jiang, Q.-Y.; Bai, X.-F.; Li, Z.; Xu, Z.; Xu, L.-W. ChemCatChem 2016, 8, 1495.
doi: 10.1002/cctc.201600084
Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
doi: 10.1021/ja980030q
Evans, P. A.; Kennedy, L. J. Org. Lett. 2000, 2, 2213.
doi: 10.1021/ol005953g
Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609.
doi: 10.1021/ja015531h
Evans, P. A.; Kennedy, L. J. J. Am. Chem. Soc. 2001, 123, 1234.
doi: 10.1021/ja005689m
Ashfeld, B. L.; Miller, K. A.; Martin, S. F. Org. Lett. 2004, 6, 1321.
doi: 10.1021/ol0496529
Plietker, B. Angew. Chem., Int. Ed. 2006, 45, 1469.
doi: 10.1002/(ISSN)1521-3773
Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467.
doi: 10.1039/c2cs35024f
Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
doi: 10.1039/C5CS00144G
Tsuji, J.; Kiji, J.; Imamura, S.; Morikawa, M. J. Am. Chem. Soc. 1964, 86, 4350.
doi: 10.1021/ja01074a023
Miyata, K.; Kutsuna, H.; Kawakami, S.; Kitamura, M. Angew. Chem., Int. Ed. 2011, 50, 4649.
doi: 10.1002/anie.201100772
Kita, Y.; Kavthe, R. D.; Oda, H.; Mashima, K. Angew. Chem., Int. Ed. 2016, 55, 1098.
doi: 10.1002/anie.201508757
Kita, Y.; Sakaguchi, H.; Hoshimoto, Y.; Nakauchi, D.; Nakahara, Y.; Carpentier, J.-F.; Ogoshi, S.; Mashima, K. Chem. Eur. J. 2015, 21, 14571.
doi: 10.1002/chem.201502329
Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. Angew. Chem., Int. Ed. 2016, 55, 16092.
doi: 10.1002/anie.201609960
Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901.
doi: 10.1021/ja803452p
Young, A. J., White, M. C. J. Am. Chem. Soc. 2008, 130, 14090.
doi: 10.1021/ja806867p
Trost, B. M.; Thaisrivongs, D. A.; Donckele E. J. Angew. Chem., Int. Ed. 2013, 52, 1523.
doi: 10.1002/anie.201207870
Chen, G.-H.; Chen, K.; Shi, Z.-J. ChemCatChem 2013, 5, 1289.
doi: 10.1002/cctc.v5.6
Trost, B. M.; Jäkel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438.
doi: 10.1021/ja029190z
Trost, B. M.; Simas, A. B. C.; Plietker, B.; Jäkel, C.; Xie, J. Chem. Eur. J. 2005, 11, 7075.
doi: 10.1002/(ISSN)1521-3765
Li, C.; Breit, B. J. Am. Chem. Soc. 2014, 136, 862.
doi: 10.1021/ja411397g
Li, C.; Grugel, C. P.; Breit, B. Chem. Commun. 2016, 52, 5840.
doi: 10.1039/C6CC02272C
Beck, T. M.; Breit, B. Eur. J. Org. Chem. 2016, 2016, 5839.
doi: 10.1002/ejoc.v2016.35
Beck, T. M.; Breit, B. Org. Lett. 2016, 18, 124.
doi: 10.1021/acs.orglett.5b03391
Beck, T. M.; Breit, B. Angew. Chem., Int. Ed. 2017, 56, 1903.
doi: 10.1002/anie.201610577
Servi, S. Synthesis 1990, 1.
Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
doi: 10.1021/cr00013a016
Fraga, C. A. M.; Barreiro, E. J. Chirality 1996, 8, 305.
doi: 10.1002/(ISSN)1520-636X
Han, Z.; Wang, Z.; Ding, K. Adv. Synth. Catal. 2011, 353, 1584.
doi: 10.1002/adsc.201100089
Chattopadhyay, A. K.; Ly, V. L.; Jakkepally, S.; Berger, G.; Hanessian, S. Angew. Chem., Int. Ed. 2016, 55, 2577.
doi: 10.1002/anie.201510861
Trost, B. M.; Schroeder, G. M. Chem. Eur. J. 2005, 11, 174.
doi: 10.1002/(ISSN)1521-3765
Trost, B. M.; Xu, J. Y.; Schmidt, T. J. Am. Chem. Soc. 2009, 131, 18343.
doi: 10.1021/ja9053948
Trost, B. M.; Osipov, M.; Dong, G. Org. Lett. 2010, 12, 1276.
doi: 10.1021/ol100167w
Trost, B. M.; Schäffner, B.; Osipov, M.; Wilton, D. A. A. Angew. Chem., Int. Ed. 2011, 50, 3548.
doi: 10.1002/anie.201007803
de Oliveira, M. N.; Fournier, J.; Arseniyadis, S.; Cossy, J. Org. Lett. 2017, 19, 14.
doi: 10.1021/acs.orglett.6b02971
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