Citation: Wu Dunqi, Cheng Xuan, Liu Yankai, Cheng Guo, Guan Xiaoyu, Deng Qinghai. A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3362-3370. doi: 10.6023/cjoc202005090 shu

A New Class of Chiral Pincer-Type PNN Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation

The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234

Corresponding author: Deng Qinghai, qinghaideng@shnu.edu.cn
Received Date: 30 May 2020
Revised Date: 16 June 2020
Available Online: 8 July 2020
Fund Project: the Shanghai Engineering Research Center of Green Energy Chemical Engineering 18DZ2254200the National Natural Science Foundation of China 21772122Project supported by the National Natural Science Foundation of China (Nos. 21402119, 21772122) and the Shanghai Engineering Research Center of Green Energy Chemical Engineering (No. 18DZ2254200)the National Natural Science Foundation of China 21402119

Figures(2)

tridentate P, N, N-donor pincer ligands bearing two or three stereocenters, 1-(4, 5-dihydro-oxazol-2-yl)-N-(2-(diphenylphosphanyl)benzyl)methanamines (oxpma), were synthesized starting from readily available amino acids in five or six steps. They were applied in palladium-catalyzed asymmetric allylic alkylation of allylic acetates to afford the desired products with high enantioselectivities (up to 96% ee).
- PNN ligand,
- pincer ligand,
- asymmetric catalysis,
- asymmetric allylic alkylation
1. [1]
  For selected books and reviewes on chiral pincer ligands, see: (a) Liu, J.-K.; Gong, J.-F.; Song, M.-P. Org. Biomol. Chem. 2019, 17, 6069.
  (b) Morales-Morales, D. Pincer Compounds: Chemistry and Applications, Elsevier, Amsterdam, 2018.
  (c) Asay, M.; Morales-Morales, D. Dalton Trans. 2015, 44, 17432.
  (d) Deng, Q.-H.; Melen, R. L.; Gade, L. H. Acc. Chem. Res. 2014, 47, 3162.
  (e) Szabó, K. L.; Wendt, O. F. Pincer and Pincer-Type Complexes, Wiley-VCH, Weinheim, 2014.
2. [2]
  (a) Hua, Y.-Y.; Bin, H.-Y.; Wei, T.; Cheng, H.-A.; Lin, Z.-P.; Fu, X.-F.; Li, Y.-Q.; Xie, J.-H.; Yan, P.-C.; Zhou, Q.-L. Org. Lett. 2020, 22, 818.
  (b) Gu, X.-S.; Yu, N.; Yang, X.-H.; Zhu, A.-T.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2019, 21, 4111.
  (c) Chen, G.-Q.; Lin, B.-J.; Huang, J.-M.; Zhao, L.-Y.; Chen, Q.-S.; Jia, S.-P.; Yin, Q.; Zhang, X. J. Am. Chem. Soc. 2018, 140, 8064.
  (d) Zhang, Y.-M.; Yuan, M.-L.; Liu, W.-P.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2018, 20, 4486.
  (e) Liu, Y.-T.; Chen, J.-Q.; Li, L.-P.; Shao, X.-Y.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2017, 19, 3231.
  (f) Zhu, G.-L.; Zhang, X.-D.; Yang, L.-J.; Xie, J.-H.; Che, D.-Q.; Zhou, Q.-L.; Yan, P.-C.; Li, Y.-Q. Org. Process Res. Dev. 2016, 20, 81.
  (g) Yan, P.-C.; Xie, J.-H.; Zhang, X.-D.; Chen, K.; Li, Y.-Q.; Zhou, Q.-L.; Che, D.-Q. Chem. Commun. 2014, 50, 15987.
  (h) Yang, X.-H.; Wang, K.; Zhu, S.-F.; Xie, J.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2014, 136, 17426.
  (i) Yang, X.-H.; Xie, J.-H.; Zhou, Q.-L. Org. Chem. Front. 2014, 1, 190.
  (j) Yan, P.-C.; Zhu, G.-L.; Xie, J.-H.; Zhang, X.-D.; Zhou, Q.-L.; Li, Y.-Q.; Shen, W.-H.; Che, D.-Q. Org. Process Res. Dev. 2013, 17, 307.
  (k) Zhang, Q.-Q.; Xie, J.-H.; Yang, X.-H.; Xie, J.-B.; Zhou, Q.-L. Org. Lett. 2012, 14, 6158.
  (l) Xie, J.-H.; Liu, X.-Y.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 7329.
3. [3]
  Zhang, F.-H.; Wang, C.; Xie, J.-H.; Zhou, Q.-L. Adv. Synth. Catal. 2019, 361, 2832. doi: 10.1002/adsc.201900251
4. [4]
  Zhang, L.; Tang, Y.; Han, Z.; Ding, K. Angew.Chem., Int.Ed. 2019, 58, 4973. doi: 10.1002/anie.201814751
5. [5]
  (a) Yamamura, T.; Nakane, S.; Nomura, Y.; Tanaka, S.; Kitamura, M. Tetrahedron 2016, 72, 3781.
  (b) Yamamura, T.; Nakatsuka, H.; Tanaka, S.; Kitamura, M. Angew. Chem., Int. Ed. 2013, 52, 9313.
6. [6]
  (a) Ling, F.; Chen, J.; Nian, S.; Hou, H.; Yi, X.; Wu, F.; Xu, M.; Zhong, W. Synlett 2020, 31, 285.
  (b) Qin, C.; Hou, C.-J.; Liu, H.; Liu, Y.-J.; Huang, D.-Z.; Hu, X.-P. Tetrahedron Lett. 2018, 59, 719.
  (c) Widegren, M. B.; Harkness, G. J.; Slawin, A. M. Z.; Cordes, D. B.; Clarke, M. L. Angew. Chem., Int. Ed. 2017, 56, 5825.
  (d) Chen, X.-S.; Hou, C.-J.; Qin, C.; Liu, H.; Liu, Y.-J.; Huang, D.-Z.; Hu, X.-P. RSC Adv. 2017, 7, 12871.
  (e) Hou, C.-J.; Hu, X.-P. Org. Lett. 2016, 18, 5592.
  (f) Nie, H.; Zhou, G.; Wang, Q.; Chen, W.; Zhang, S. Tetrahedron: Asymmetry 2013, 24, 1567.
  (g) Yamamura, T.; Nakatsuka, H.; Tanaka, S.; Kitamura, M. Angew. Chem., Int. Ed. 2013, 52, 9313.
7. [7]
  (a) Gu, G.; Hu, Y.; Liu, S.; Dong, X.-Q.; Zhang, X. Chin. J. Org. Chem. 2020, 40, 997(in Chinese).
  (古国贤, 胡杨, 刘绍东, 董秀琴, 张绪穆, 有机化学, 2020, 40, 997.)
  (b) Gu, G.; Yang, T.; Yu, O.; Qian, H.; Wang, J.; Wen, J.; Dang, L.; Zhang, X. Org. Lett. 2017, 19, 5920.
  (c) Wu, W.; You, C.; Yin, C.; Liu, Y.; Dong, X.-Q.; Zhang, X. Org. Lett. 2017, 19, 2548.
  (d) Wu, W.; Liu, S.; Duan, M.; Tan, X.; Chen, C.; Xie, Y.; Lan, Y.; Dong, X.-Q.; Zhang, X. Org. Lett. 2016, 18, 2938.
8. [8]
  (a) Demmans, K. Z.; Olson, M. E.; Morris, R. H. Organometallics 2018, 37, 4608.
  (b) Díaz-Valenzuela, M. B.; Phillips, S. D.; France, M. B.; Gunn, M. E.; Clarke, M. L. Chem.-Eur. J. 2009, 15, 1227.
9. [9]
  Liu, H.; Yuan, H.; Shi, X. Dalton Trans. 2019, 48, 609. doi: 10.1039/C8DT04413A
10. [10]
  (a) Blasius, C. K.; Ren, B.-T.; Bürgy, D.; Liu, Y.-K.; Li, B.; Michalsky, I.; Wadepohl, H.; Deng, Q.-H.; Gade, L. H. J. Org. Chem. 2020, 85, 6719.
  (b) Wang, C.-J.; Sun, J.; Zhou, W.; Xue, J.; Ren, B.-T.; Zhang, G.-Y.; Mei, Y.-L.; Deng, Q.-H. Org. Lett. 2019, 21, 7315.
  (c) Bleith, T.; Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Angew. Chem., Int. Ed. 2016, 55, 7852.
  (d) Deng, Q.-H.; Rettenmeier, C.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2014, 20, 93.
  (e) Deng, Q.-H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356.
  (f) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 2946.
  (g) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769.
  (h) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2011, 17, 14922.
11. [11]
  For selected reviewes on chiral oxazoline-containing ligands, see: (a) Liu, X.; Chen, P.; Wu, F. Chin. J. Org. Chem. 2016, 36, 1797(in Chinese).
  (刘小建, 陈品红, 吴范宏, 有机化学, 2016, 36, 1797.)
  (b) Liu, L.; Ma, H.; Wu, Y.; Yuan, D.; Liu, J.; Fu, B.; Ma, X. Chin. J. Org. Chem. 2013, 33, 2283(in Chinese).
  (刘磊, 麻红利, 吴燕华, 袁德凯, 刘吉平, 傅滨, 马晓东, 有机化学, 2013, 33, 2283.)
  (c) Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2011, 111, PR284.
  (d) Rasappan, R.; Laventine, D.; Reiser, O. Coord. Chem. Rev. 2008, 252, 702.
  (e) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
12. [12]
  For selected reviewes and examples on metal-catalyzed asymmetric allylic alkylation, see: (a) Cheng, Q.; Tu, H.-F.; Zheng, C.; Qu, J.-P.; Helmchen, G.; You, S.-L. Chem. Rev. 2019, 119, 1855.
  (b) James, J.; Jackson, M.; Guiry, P. J. Adv. Synth. Catal. 2019, 361, 3016.
  (c) Yu, F.-L.; Bai, D.-C.; Liu, X.-Y.; Jiang, Y.-J.; Ding, C.-H.; Hou, X.-L. ACS Catal. 2018, 8, 3317.
  (d) Farkas, G.; Császár, Z.; Stágel, K.; Nemes, E.; Balogh, S.; Tóth, I.; Bényei, A.; Lendvay, G.; Bakos, J. J. Organomet. Chem. 2017, 846, 129.
  (e) Jiang, Y.-J.; Zhang, G.-P.; Huang, J.-Q.; Chen, D.; Ding, C.-H.; Hou, X.-L. Org. Lett. 2017, 19, 5932.
  (f) Zheng, N.; Song, W. Chin. J. Org. Chem. 2017, 37, 1099(in Chinese).
  (郑楠, 宋汪泽, 有机化学, 2017, 37, 1099.)
  (g) Fu, J.; Huo, X.; Li, B.; Zhang, W. Org. Biomol. Chem. 2017, 15, 9747.
  (h) Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
  (i) Bai, D.-C.; Yu, F.-L.; Wang, W.-Y.; Chen, D.; Li, H.; Liu, Q.-R.; Ding, C.-H.; Chen, B.; Hou, X.-L. Nat. Commun. 2016, 7, 11806.
  (j) Bai, D.-C.; Wang, W.-Y.; Ding, C.-H.; Hou, X.-L. Synlett 2015, 26, 1510.
  (k) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
  (l) Ding, C.-H.; Hou, X.-L. Top. Organomet. Chem. 2011, 36, 247.
  (m) You, S.-L.; Dai, L.-X. Angew. Chem., Int. Ed. 2006, 45, 5246.
  (n) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
13. [13]
  Singh, S. P.; Michaelides, A.; Merrill, A. R.; Schwan, A. L. J. Org. Chem. 2011, 76, 6825. doi: 10.1021/jo2008093
14. [14]
  Qi, M.-H.; Wang, F.-J.; Shi, M. Tetrahedron:Asymmetry 2010, 21, 247. doi: 10.1016/j.tetasy.2010.02.003
15. [15]
  Li, X.; Taechalertpaisarn, J.; Xin, D.; Burgess, K. Org. Lett. 2015, 17, 632. doi: 10.1021/ol5036547
16. [16]
  (a) Miao, C.; Wang, B.; Wang, Y.; Xia, C.; Lee, Y.-M.; Nam, W.; Sun, W. J. Am. Chem. Soc. 2016, 138, 936.
  (b) Steinig, A. G.; Spero, D. M. J. Org. Chem. 1999, 64, 2406.
17. [17]
  Wang, Y.; Du, S.; Armstrong, D. W. Anal. Bioanal. Chem. 2018, 410, 4725. doi: 10.1007/s00216-018-0901-5
18. [18]
  Gagnon, D.; Lauzon, S.; Godbout, C.; Spino, C. Org. Lett. 2005, 7, 4769. doi: 10.1021/ol052034n
19. [19]
  Lee, J.-Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837. doi: 10.1021/ol050528e
20. [20]
  Jung, B.; Kang, S. H. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 1471. doi: 10.1073/pnas.0607865104
21. [21]
  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, 2873. doi: 10.1039/C3CC49488H
22. [22]
  Jayakumar, S.; Prakash, M.; Balaraman, K.; Kesavan, V. Eur. J. Org. Chem. 2014, 606.
23. [23]
  Hao, X.-Q.; Dong, Y.-N.; Gao, B.; Li, K.; Zhao, X.-M.; Xu, Y.; Song, M.-P. Tetrahedron:Asymmetry 2015, 26, 1360. doi: 10.1016/j.tetasy.2015.10.007
24. [24]
  Jin, Y.; Du, D.-M. Tetrahedron 2012, 68, 3633 doi: 10.1016/j.tet.2012.02.078
25. [25]
  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
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