Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions with Allylic Esters
- Corresponding author: Yang Dingqiao, yangdq@scnu.edu.cn
Citation:
Deng Yingying, Yang Wen, Yang Xin, Yang Dingqiao. Progress in Iridium-Catalyzed Asymmetric Allylic Substitution Reactions with Allylic Esters[J]. Chinese Journal of Organic Chemistry,
;2017, 37(12): 3039-3059.
doi:
10.6023/cjoc201704034
(a) Liu, Z.-Q.; Du, H.-F. Org. Lett. 2010, 12, 3054.
(b) Zhang, P.; Le, H.; Kyne, R. E.; Morken, J. P. J. Am. Chem. Soc. 2011, 133, 9716.
(c) Suetsugu, S.; Nishiguchi, H.; Tsukano, C.; Takemoto, Y. Org. Lett. 2014, 16, 996.
(d) Katcher, M. H.; Norrby, P. O.; Doyle, A. G. Organometallics 2014, 33, 2121.
(a) Hughes, D. L.; Lloyd-Jones, G. C.; Krska, S. W.; Gouriou, L.; Bonnet, V. D.; Jack, K.; Sun, Y.-K.; David, J. M.; Reamer, R. A. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5379.
(b) Litto, R. D.; Benessere, V.; Ruffo, F.; Moberg, C. Eur. J. Org. Chem. 2009, 1352.
Moberg, C. Top Organomet. Chem. 2012, 38, 209.
(a) Jegelka, M.; Plietker, B. Org. Lett. 2009, 11, 3462.
(b) Jegelka, M.; Plietker, B. Chem. Eur. J. 2011, 17, 10417.
(a) Trost, B. M.; Rao, M.; Dieskau, A. P. J. Am. Chem. Soc. 2013, 135, 18697.
(b) Kawatsura, M.; Uchida, K.; Terasaki, S.; Tsuji, H.; Minakawa, M.; Itoh, T. Org. Lett. 2014, 16, 1470.
Tan, Z.-Z.; Wan, X.-L.; Zang, Z.-H.; Qian, Q.; Deng, W.; Gong, H.-G. Chem. Commun. 2014, 50, 3827.
doi: 10.1039/C3CC49859J
(a) Vrieze, D. C.; Hoge, G. S.; Hoerter, P. Z.; Van Haitsma, J. T.; Samas, B. M. Org. Lett. 2009, 11, 3140.
(b) Arnold, J. S.; Nguyen, H. M. J. Am. Chem. Soc. 2012, 134, 8380.
(a) Yang, S.-C.; Feng, W.-H.; Gan, K.-H. Tetrahedron 2006, 62, 3752.
(b) Zhang, M.; Watanabe, K. J.; Tsukamoto, M.; Shibuya, R.; Morimoto, H.; Ohshima, T. Chem.-Eur. J. 2015, 21, 1.
Guduguntla, S.; Hornillos, V.; Tessier, R.; Fañanás-Mastral, M.; Feringa, B. L. Org. Lett. 2016, 18, 252.
doi: 10.1021/acs.orglett.5b03396
Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147.
doi: 10.1039/c2ob07086c
Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
doi: 10.1021/ar500167f
Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
doi: 10.1021/acscatal.6b01886
Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. 1997, 36, 263.
doi: 10.1002/(ISSN)1521-3773
Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
doi: 10.1016/S0040-4039(97)10220-9
Butt, N. A.; Zhang, W.-B. Chem. Soc. Rev. 2015, 44, 7929.
doi: 10.1039/C5CS00144G
Helmchen, G.; Dahnz, A.; Dubon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675.
Wu, Y.-J.; Long, Y.-H.; Yang, D.-Q. Chin. J. Org. Chem. 2009, 29, 1522(in Chinese).
Giacomina, F.; Riat, D.; Alexakis, A. Org. Lett. 2010, 12, 1156.
doi: 10.1021/ol100162y
Stanley, L. M.; Bai, C.; Ueda, M.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 8918.
doi: 10.1021/ja103779e
Zhao, Z.-L.; Gu, Q.; Wu, X.-Y.; You, S.-L. Chin. Chem. Lett. 2016, 27, 619.
doi: 10.1016/j.cclet.2016.02.017
Bondzic, B. P.; Farwick, A.; Liebich, J.; Eilbracht, P. Org. Biomol. Chem. 2008, 6, 3723.
doi: 10.1039/b809143a
Liu, W.-B.; Zheng, S.-C.; He, H.; Zhao, X.-M.; Dai, L.-X.; You, S.-L. Chem. Commun. 2009, 6604.
Zhang, H.-B.; Chen, J.-T.; Zhao, X.-M. Org. Biomol. Chem. 2016, 14, 7183.
doi: 10.1039/C6OB01246A
Liu, W.-B.; Zheng, C.; Zhuo, C.-X.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2012, 134, 4812.
doi: 10.1021/ja210923k
Xu, Q.-L.; Dai, L.-X.; You, S.-L. Adv. Synth. Catal. 2012, 354, 2275.
doi: 10.1002/adsc.v354.11/12
Zhan, M.; Li, R.-Z.; Mou, Z.-D.; Cao, C.-G.; Liu, J.; Chen, Y.-W.; Niu, D.-W. ACS Catal. 2016, 6, 3381.
doi: 10.1021/acscatal.6b00719
(a) Trost, B. M.; Jiang, C. H. Synthesis 2006, 369.
(b) Behenna, D. C.; Stoltz, B. M. Top Organomet. Chem. 2013, 44, 281.
Chen, W.-Y.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068.
doi: 10.1021/ja311363a
Chen, W.-Y.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 377.
doi: 10.1021/ja410650e
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
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
Liu, J.; Cao, C.-G.; Sun, H.-B.; Zhang, X.; Niu, D.-W. J. Am. Chem. Soc. 2016, 138, 13103.
doi: 10.1021/jacs.6b05288
(a) Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020.
(b) Sandmeier, T.; Krautwald, S.; Zipfel, H. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363.
(a) Yao, K.; Liu, D.-L.; Yuan, Q.-J.; Imamoto, T.; Liu, Y.-G.; Zhang, W.-B. Org. Lett. 2016, 18, 6296.
(b) Huo, X.-H.; Yang, G.-Q.; Liu, D.-L.; Liu, Y.-G.; Gridnev, I. D.; Zhang, W.-B. Angew. Chem., Int. Ed. 2014, 53, 6776.
Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065.
doi: 10.1126/science.1237068
Wei, X.; Liu, D.-L.; An, Q.-J.; Zhang, W.-B. Org. Lett. 2015, 17, 5768.
doi: 10.1021/acs.orglett.5b02868
Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Org. Lett. 2008, 10, 1815.
doi: 10.1021/ol800409d
Zhou, C.-X.; Wu, Q.-F.; Zhou, Q.; Xu, Q.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 8169.
doi: 10.1021/ja403535a
Zhuo, C.-X.; Cheng, Q.; Liu, W.-B.; Zhao, Q.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 8475.
doi: 10.1002/anie.201502259
Wu, Q.-F.; Liu, W.-B.; Zhuo, C.-X.; Rong, Z.-Q.; Ye, K.-Y.; You, S.-L. Angew. Chem., Int. Ed. 2011, 50, 4455.
doi: 10.1002/anie.201100206
Xu, Q.-L.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 2579.
doi: 10.1021/ol3008793
Cheng, Q.; Wang, Y.; You, S.-L. Angew. Chem., Int. Ed. 2016, 55, 3496.
doi: 10.1002/anie.201511519
Chen, W.-Y.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 15249.
doi: 10.1021/ja306850b
Chen, W.-Y.; Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 15825.
doi: 10.1021/ja506500u
Chen, M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2014, 53, 8691.
doi: 10.1002/anie.201403844
Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 13972.
doi: 10.1021/jacs.5b09980
Chen, M.:Hartwig, J. F. Angew. Chem., Int. Ed. 2014, 53, 12172.
doi: 10.1002/anie.201406778
Chen, M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 11651.
doi: 10.1002/anie.201607053
Jiang, X.-Y.; Chen, W.-Y.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 5819.
doi: 10.1002/anie.201600235
Alexakis, A.; Hajjaji, S. E.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393.
doi: 10.1021/ol0713842
Polet, D.; Rathgeb, X.; Falciola, C. A.; Langlois, J. B.; Hajjaji, S. E.; Alexakis, A. Chem. Eur. J. 2009, 15, 1205.
doi: 10.1002/chem.200801879
Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 7644.
doi: 10.1002/anie.201501851
Liu, X.-J.; You, S.-L. Angew. Chem., Int. Ed. 2017, 56, 4002.
doi: 10.1002/anie.201700433
Breitler, S.; Carreira, E. M. J. Am. Chem. Soc. 2015, 137, 5296.
doi: 10.1021/jacs.5b01951
Pouy, M. J.; Leitner, A.; Weix, D. J.; Ueno, S.; Hartwig, J. F. Org. Lett. 2007, 9, 3949.
doi: 10.1021/ol701562p
Pouy, M. J.; Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 11312.
doi: 10.1021/ja905059r
Weihofen, R.; Tverskoy, O.; Helmchen, G. Angew. Chem., Int. Ed. 2006, 45, 5546.
doi: 10.1002/(ISSN)1521-3773
Spiess, S.; Berthold, C.; Weihofen, R.; Helmchen, G. Org. Biomol. Chem. 2007, 5, 2357.
doi: 10.1039/B708571K
Weix, D. J.; Markovic, D.; Ueda, M.; Hartwig, J. F. Org. Lett. 2009, 11, 2944.
doi: 10.1021/ol901151u
Markovic, D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 11680.
doi: 10.1021/ja074584h
Ye, K.-Y.; Dai, L.-X.; You, S.-L. Org. Biomol. Chem. 2012, 10, 5932.
doi: 10.1039/c2ob00036a
Ye, K.-Y.; Dai, L.-X.; You, S.-L. Chem. Eur. J. 2014, 20, 3040.
doi: 10.1002/chem.201400026
Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 8971.
doi: 10.1021/ja902243s
Liu, W.-B.; Zhang, X.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 5183.
doi: 10.1002/anie.201200649
Yang, Z.-P.; Wu, Q.-F.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 6986.
doi: 10.1002/anie.201404286
Zhang, X.; Yang, Z.-P.; Huang, L.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 1873
doi: 10.1002/anie.201409976
Yang, Z.-P.; Wu, Q.-F.; Shao, W.; You, S.-L. J. Am. Chem. Soc. 2015, 137, 15899.
doi: 10.1021/jacs.5b10440
Zhuo, C.-X.; Zhang, X.; You, S.-L. ACS Catal. 2016, 6, 5307.
doi: 10.1021/acscatal.6b01585
Ye, K.-Y.; Cheng, Q.; Zhuo, C.-X.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2016, 55, 8113.
doi: 10.1002/anie.201603266
Yang, Z.-P.; Zheng, C.; Huang, L.; Qian, C.; You, S.-L. Angew. Chem., Int. Ed. 2017, 56, 1530.
doi: 10.1002/anie.201611056
Miyabe, H.; Yoshida, K.; Reddy, V. K.; Takemoto, Y. J. Org. Chem. 2009, 74, 305.
doi: 10.1021/jo802271d
Gärtner, M.; Jäkel, M.; Achatz, M.; Sonnenschein, C.; Tverskoy, O.; Helmchen, G. Org. Lett. 2011, 13, 2810.
doi: 10.1021/ol200688d
Lee, J.-H.; Lee, S.-G. Chem. Sci. 2013, 4, 2922.
doi: 10.1039/c3sc50901j
Satyanarayana, G.; Helmchen, G. Eur. J. Org. Chem. 2014, 2242.
Grange, R. L.; Clizbe, E. A.; Counsell, E. J.; Evans, A. P. Chem. Sci. 2015, 6, 777.
doi: 10.1039/C4SC01317D
Kimura, M.; Uozumi, Y. J. Org. Chem. 2007, 72, 707.
doi: 10.1021/jo0615403
He, H.; Ye, K.-Y.; Wu, Q.-F.; Dai, L.-X.; You, S.-L. Adv. Synth. Catal. 2012, 354, 1084.
doi: 10.1002/adsc.201100809
Qu, J.-P.; Roβberg, L.; Helmchen, G. J. Am. Chem. Soc. 2014, 136, 1272.
doi: 10.1021/ja411869r
Zhao, D.-P.; Martin, F. M.; Chang, M.-C.; Otten, E.; Feringa, B. L. Chem. Sci. 2014, 5, 4216.
doi: 10.1039/C4SC01940G
Zheng, S.-C.; Zhang, M.; Zhao. X.-M. Chem. Eur. J. 2014, 20, 1.
doi: 10.1002/chem.201390210
Zhang, M.; Zheng, S.-C.; Zhao, X.-M. Chem. Commun. 2014, 50, 4455.
doi: 10.1039/c4cc00413b
Gärtner, M.; Mader, S.; Seehafer, K.; Helmchen, G. J. Am. Chem. Soc. 2011, 133, 2072.
doi: 10.1021/ja109953v
Xu, Q.-L.; Dai, L.-X.; You, S.-L. Org. Lett. 2010, 12, 800.
doi: 10.1021/ol902873q
Ueda, M.; Hartwing, J. F. Org. Lett. 2010, 12, 92.
doi: 10.1021/ol9023248
Liu, W.; Zhao, X.-M.; Zhang, H.-B.; Zhang, L.; Zhao, M.-Z. Chem. Eur. J. 2014, 20, 16873.
doi: 10.1002/chem.201405058
Zheng, S.-C.; Gao, N.; Liu, W.; Liu, D.-G.; Zhao, X.-M.; Cohen, T. Org. Lett. 2010, 12, 4454.
doi: 10.1021/ol101915b
Zheng, S.-C.; Huang, W.-Q.; Gao, N.; Cui, R.-M.; Zhang, M.; Zhao, X.-M. Chem. Commum. 2011, 47, 6969.
doi: 10.1039/c1cc11930c
Huang, W.-Q.; Zheng, S.-C.; Tang, J.-L.; Zhao, X.-M. Org. Biomol. Chem. 2011, 9, 7897.
doi: 10.1039/c1ob06332d
Gao, N.; Zhao, X.-M. Eur. J. Org. Chem. 2013, 2708.
Topczewski, J. J.; Tewson, T. J.; Nguyen, H. M. J. Am. Chem. Soc. 2011, 133, 19318.
doi: 10.1021/ja2087213
Zhang, Q.; Stockdale, D. P.; Mixdorf, J. C.; Topczewski, J. J.; Nguyen, H. M. J. Am. Chem. Soc. 2015, 137, 11912.
doi: 10.1021/jacs.5b07492
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