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

doi:10.6023/cjoc202005090

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3362-3370.DOI: 10.6023/cjoc202005090 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

新型手性钳形PNN类配体在钯催化不对称烯丙基烷基化反应中的应用

吴敦奇, 成轩, 刘炎开, 成果, 管笑宇, 邓清海

上海师范大学教育部资源化学重点实验室和上海市稀土功能材料重点实验室上海 200234

收稿日期:2020-05-30 修回日期:2020-06-16 发布日期:2020-07-09
通讯作者: 邓清海 E-mail:qinghaideng@shnu.edu.cn
基金资助:
国家自然科学基金（Nos.21402119，21772122）和上海绿色能源化工工程技术研究中心（No.18DZ2254200）资助项目.

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

Wu Dunqi, Cheng Xuan, Liu Yankai, Cheng Guo, Guan Xiaoyu, Deng Qinghai

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

Received:2020-05-30 Revised:2020-06-16 Published:2020-07-09
Supported by:
Project 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).

1. cjoc202005090.pdf(4872KB)

Abstract

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).

Key words: PNN ligand, pincer ligand, asymmetric catalysis, asymmetric allylic alkylation

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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] (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] Zhang, F.-H.; Wang, C.; Xie, J.-H.; Zhou, Q.-L. Adv. Synth. Catal. 2019, 361, 2832.
[4] Zhang, L.; Tang, Y.; Han, Z.; Ding, K. Angew. Chem., Int. Ed. 2019, 58, 4973.
[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] (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] (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] (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] Liu, H.; Yuan, H.; Shi, X. Dalton Trans. 2019, 48, 609.
[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] 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] 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] Singh, S. P.; Michaelides, A.; Merrill, A. R.; Schwan, A. L. J. Org. Chem. 2011, 76, 6825.
[14] Qi, M.-H.; Wang, F.-J.; Shi, M. Tetrahedron:Asymmetry 2010, 21, 247.
[15] Li, X.; Taechalertpaisarn, J.; Xin, D.; Burgess, K. Org. Lett. 2015, 17, 632.
[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] Wang, Y.; Du, S.; Armstrong, D. W. Anal. Bioanal. Chem. 2018, 410, 4725.
[18] Gagnon, D.; Lauzon, S.; Godbout, C.; Spino, C. Org. Lett. 2005, 7, 4769.
[19] Lee, J.-Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837.
[20] Jung, B.; Kang, S. H. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 1471.
[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.
[22] Jayakumar, S.; Prakash, M.; Balaraman, K.; Kesavan, V. Eur. J. Org. Chem. 2014, 606.
[23] Hao, X.-Q.; Dong, Y.-N.; Gao, B.; Li, K.; Zhao, X.-M.; Xu, Y.; Song, M.-P. Tetrahedron:Asymmetry 2015, 26, 1360.
[24] Jin, Y.; Du, D.-M. Tetrahedron 2012, 68, 3633
[25] Xu, J.-X.; Ye, F.; Bai, X.-F.; Zhang, J.; Xu, Z.; Zheng, Z.-J.; Xu, L.-W. RSC Adv. 2016, 6, 45495.

新型手性钳形PNN类配体在钯催化不对称烯丙基烷基化反应中的应用

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[3]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[4]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[7]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[8]	Siqiang Fang, Zanjiao Liu, Tianli Wang. Recent Advances of the Atherton-Todd Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1069-1083.
[9]	Yan Zeng, Fei Ye. Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3388-3413.
[10]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[11]	Xin Kuang, Changhua Ding, Yichen Wu, Peng Wang. Catalytic Enantioselective Preparation of Chiral Allylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3367-3387.
[12]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.
[13]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[14]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[15]	Yunrong Chen, Wei Liu, Xiaoyu Yang. Recent Advances in Kinetic Resolution of Tertiary Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 679-697.