Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles

doi:10.6023/A18060238

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (11): 862-868.DOI: 10.6023/A18060238 Previous Articles Next Articles

Special Issue: 有机小分子-金属协同催化

Communication

Au(I)/手性双功能叔胺催化实现的一锅法串联成烯/不对称环化反应构建螺环季碳氧化吲哚

廖富民^a, 杜溢^b, 周锋^a, 周剑^a,c,d

a. 绿色化学与化工过程绿色化上海市重点实验室华东师范大学化学与分子工程学院上海 200062;
b. 上海交通大学医学院附属新华医院上海 200032;
c. 上海分子治疗与新药创制工程技术研究中心华东师范大学化学与分子工程学院上海 200062;
d. 金属有机化学国家重点实验室中国科学院上海有机化学研究所上海 200032

投稿日期:2018-06-18 发布日期:2018-07-23
通讯作者: 周剑 E-mail:jzhou@chem.ecnu.edu.cn
基金资助:
项目受国家自然科学基金（No.21472049）资助.

Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles

Liao Fumin^a, Du Yi^b, Zhou Feng^a, Zhou Jian^a,c,d

a. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062;
b. Xinhua Hospital, Affiliated to Shanghai Jiaotong University School of Medicine, Shanghai 200032;
c. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062;
d. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032

Received:2018-06-18 Published:2018-07-23
Contact: 10.6023/A18060238 E-mail:jzhou@chem.ecnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21472049).

1. Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles.PDF(3205KB)

Abstract

We report an asymmetric tandem reaction realized by sequential Au(I)/chiral bifunctional tertiary amine catalysis. A tandem olefination/asymmetric cyclization reaction is developed, allowing facile synthesis of quaternary spirocyclic oxindoles in good yields and stereoselectivities from N-Ac protected diazooxindoles 1, monofluorinated enol silyl ethers 2 and 2-tosylaminochalcone 4. The initial cross coupling reaction of diazooxindole and fluorinated enol silyl ethers, catalyzed by 3.0 mol% IPrAuBF₄, readily afforded 3-alkenyloxindoles for the subsequent Michael/Michael addition of 2-tosylaminochalcone catalyzed by 5.0~10.0 mol% chiral bifunctional tertiary amine-squaramide C1. The tandem reaction was performed by the following general procedure. Under an atmosphere of N₂, to an oven-dried Schlenk tube were added IPrAuCl (6.0 mg, 0.0099 mmol, 3.3 mol%) and AgBF₄ (1.8 mg, 0.0090 mmol, 3.0 mol%), followed by anhydrous CH₂Cl₂ (1.0 mL). The resulting mixture was stirred at 25℃ for 0.5 h and then cooled down to 0℃. After ethers 2 (1.5 equiv.) was added in one-portion, a solution of diazooxindoles 1 in 1.5 mL of CH₂Cl₂ was added slowly by a syringe pump in 20 minutes. The reaction was stirred at 0℃ till full consumption of 1 by TLC analysis. After the successive addition of C1 and 4 (1.1 equiv.), the reaction was warmed to 25℃ and stirred till full consumption of 3, and the mixture was directly subjected to the column chromatography by using petroleum ether/dichloromethane (1/2.5, V/V) as the eluent to give the desired spirocyclic oxindoles 5. The diastereoselectivities of 5 (>20:1) were determined by ¹H NMR analysis of the crude reaction mixture. The key step of this tandem sequence is the cross coupling reaction of monofluorinated enol silyl ethers and donor-acceptor diazo reagents. We further examined the substrates scope of acyclic aryl diazoacetates and fluorinated enol silyl ethers by using 1.0 mol% IPrAuSbF₆ as catalyst, providing a new method for the efficient synthesis of trisubstituted alkenes.

Key words: Au (I)/Chiral tertiary amine catalysis, diazooxindoles, trisubstituted monofluorinated enol silyl ethers, quaternary spirocyclic oxindoles, trisubstituted alkenes

Cite this article

Liao Fumin, Du Yi, Zhou Feng, Zhou Jian. Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles[J]. Acta Chim. Sinica, 2018, 76(11): 862-868.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Zhou, J. Multicatalyst system in asymmetric catalysis, John Wiley & Sons, New York, 2014.
[2] For reviews:(a) Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2999.
(b) Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633.
[3] (a) Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222. For selected examples:
(b) Longmire, J.; Wang, B.; Zhang, X.-M. J. Am. Chem. Soc. 2002, 124, 13400.
(c) Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem., Int. Ed. 2006, 45, 1979.
(d) Yan, X.-X.; Peng, Q.; Li, Q.; Zhang, K.; Yao, J.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem. Soc. 2008, 130, 14362.
(e) Xu, H.; Zuend, S. J.; Woll, M. J.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986.
[4] (a) Long, J.; Ding, K. Angew. Chem., Int. Ed. 2001, 40, 544.
(b) Zhou, J.; Wakchaure, V.; Kraft, P.; List, B. Angew. Chem., Int. Ed. 2008, 47, 7656.
(c) Lv, J.; Li, X.; Zhong, L.; Luo, S.; Cheng, J.-P. Org. Lett. 2010, 12, 1096.
(d) Lv, J.; Zhang, L.; Zhou, Y.; Nie, Z.; Luo, S.; Cheng, J.-P. Angew. Chem., Int. Ed. 2011, 50, 6610.
(e) Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730.
[5] (a) Zhou, J. Chem. Asian J. 2010, 5, 422.
(b) Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211.
(c) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337.
(d) Pellissier, H. Tetrahedron 2013, 69, 7171.
(e) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365.
[6] Chen, G.-S.; Deng, Y.-J.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron:Asymmetry 2001, 12, 1567.
[7] For selected examples:(a) Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952.
(b) Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 48, 8923.
(c) Yang, T.; Ferrali, A.; Sladojevich, F.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 9140.
(d) Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
(e) Li, B.; Liu, R.; Liang, R.; Jia, Y. Acta Chim. Sinica 2017, 75, 448(in Chinese). (李保乐, 刘人荣, 梁仁校, 贾义霞, 化学学报, 2017, 75, 448.)
[8] For reviews:(a) Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem. Eur. J. 2010, 16, 9350.
(b) Wu, X.; Li, M.-L.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 1091(in Chinese). (吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.)
(c) Yang, Z.-P.; Zhang, W.; You, S.-L. J. Org. Chem. 2014, 79, 7785. For leading examples:
(d) Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448.
(e) Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336.
(f) Rueping, M.; Antonchick, A. P.; Brinkmann, C. Angew. Chem., Int. Ed. 2007, 46, 6903.
(g) Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2008, 130, 14452.
(h) Han, Z.-Y.; Xiao, H.; Chen, X.-H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182.
(i) Ren, L.; Lei, T.; Ye, J.-X.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 771.
(j) Tao, Z.-L.; Zhang, W.-Q.; Chen, D.-F.; Adele, A.; Gong, L.-Z. J. Am. Chem. Soc. 2013, 135, 9255.
(k) Wang, P.-S.; Lin, H.-C.; Zhai, Y.-J.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 12218.
(l) Zhang, Z.-J.; Tao, Z.-L.; Arafate, A.; Gong, L.-Z. Acta Chim. Sinica 2017, 75, 1196(in Chinese). (张子競, 陶忠林, 阿拉法特﹒阿地力, 龚流柱, 化学学报, 2017, 75, 1196.)
[9] For a review about NHC-catalysis, see:(a) Wang, A.; Xiao, Y.; Zhou, Y.; Xu, J.; Liu, H. Chin. J. Org. Chem. 2017, 37, 2590(in Chinese). (王翱, 肖永龙, 周宇, 徐进宜, 柳红, 有机化学, 2017, 37, 2590.) For leading examples:
(b) Lebeuf, R. I.; Hirano, K.; Glorius, F. Org. Lett. 2008, 10, 4243.
(c) Cardinal-David, B.; Raup, D. E. A.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345.
(d) Raup, D. E. A.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766.
(e) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
(f) Song, J.; Zhang, Z.-J.; Chen, S.-S.; Fan, T.; Gong, L.-Z. J. Am. Chem. Soc. 2018, 140, 3177.
[10] (a) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365.
(b) Ren, Y.-Y.; Zhu, S.-F.; Zhou, Q.-L. Org. Biomol. Chem. 2018, 16, 3087.
(c) Xu, B.; Zhu, S.-F.; Xie, X.-L.; Shen, J.-J.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 11483.
(d) Xu, B.; Zhu, S.-F.; Zuo, X.-D.; Zhang, Z.-C.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2014, 53, 3913.
(e) Xu, B.; Zhu, S.-F.; Zhang, Z.-C.; Yu, Z.-X.; Ma, Y.; Zhou, Q.-L. Chem. Sci. 2014, 5, 1442.
(f) Cheng, Q.-Q.; Xu, H.; Zhu, S.-F.; Zhou, Q.-L. Acta Chim. Sinica 2015, 73, 326(in Chinese). (程清卿, 许唤, 朱守非, 周其林, 化学学报, 2015, 73, 326.)
(g) Xu, B.; Li, M.-L.; Zuo, X.-D.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2015, 137, 8700.
(h) Guo, J.-X.; Zhou, T.; Xu, B.; Zhu, S.-F.; Zhou, Q.-L. Chem. Sci. 2016, 7, 1104.
[11] (a) Liu, X.; Lin, L.; Feng, X. Acc. Chem. Res. 2011, 44, 574.
(b) Chen, F.; Feng, X.; Qin, B.; Zhang, G.; Jiang, Y. Org. Lett. 2003, 5, 949.
(c) Li, Y.; He, B.; Qin, B.; Feng, X.; Zhang, G. J. Org. Chem. 2004, 69, 7910.
(d) Wen, Y.; Huang, X.; Huang, J.; Xiong, Y.; Qin, B.; Feng, X. Synlett 2005, 2445.
(e) Liu, Y.; Liu, X.; Xin, J.; Feng, X. Synlett 2006, 1085.
(f) Xiong, Y.; Huang, X.; Gou, S.; Huang, J.; Wen, Y.; Feng, X. Adv. Synth. Catal. 2006, 348, 538.
(g) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2007, 46, 8468.
(h) Shen, K.; Liu, X.; Li, Q.; Feng, X. Tetrahedron 2008, 64, 147.
[12] Wang, X.; Guo, P.; Han, Z.; Wang, X.; Wang, Z.; Ding, K. J. Am. Chem. Soc. 2014, 136, 405.
[13] (a) Cai, Q.; Zhao, Z.-A.; You, S.-L. Angew. Chem., Int. Ed. 2009, 48, 7428.
(b) Cai, Q.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 8666.
(c) Chen, Q.-A.; Wang, D.-S.; Zhou, Y.-G.; Duan, Y.; Fan, H.-J.; Yang, Y.; Zhang, Z. J. Am. Chem. Soc. 2011, 133, 6126.
(d) Chen, Q.-A.; Chen, M.-W.; Yu, C.-B.; Shi, L.; Wang, D.-S.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2011, 133, 16432.
(e) Chen, Q.-A.; Gao, K.; Duan, Y.; Ye, Z.-S.; Shi, L.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2012, 134, 2442.
(f) Lv, J.; Zhang, L.; Hu, S.; Cheng, J.-P.; Luo, S. Chem. Eur. J. 2012, 18, 799.
(g) Chen, L.; Zhang, L.; Lv, J.; Cheng, J.-P.; Luo, S. Chem. Eur. J. 2012, 18, 8891.
(h) Lv, J.; Zhang, L.; Luo, S.; Cheng, J.-P. Angew. Chem., Int. Ed. 2013, 52, 9786.
(i) Lu, L.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278.
[14] (a) Vaxelaire, C.; Winter, P.; Christmann, M. Angew. Chem., Int. Ed. 2011, 50, 3605.
(b) Sharma, I.; Tan, D. S. Nat. Chem. 2013, 5, 157.
[15] (a) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
(b) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
(c) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857.
(d) Liu, L. Zhang, J. Chem. Soc. Rev. 2016, 45, 506.
(e) Xia, Y.; Qiu, D.; Wang, J. Chem. Rev. 2017, 117, 13810. For some recent examples of Au(I) catalysis on release diazo reagents, see:
(f) Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 5714.
(g) Zhang, D.; Xu, G.; Ding, D.; Zhu, C.; Li, J.; Sun, J. Angew. Chem., Int. Ed. 2014, 53, 11070.
(h) Zhu, C.; Xu, G.; Liu, K.; Qiu, L.; Peng, S.; Sun, J. Chem. Commun. 2015, 51, 12768.
(i) Zhu, C.; Xu, G.; Ding, D.; Qiu, L.; Sun, J. Org. Lett. 2015, 17, 4244.
(j) Hu, M.; Ni, C.; Li, L.; Han, Y.; Hu, J. J. Am. Chem. Soc. 2015, 137, 14496.
(k) Zhang, Z.; Yu, W.; Wu, C.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2016, 55, 273.
[16] (a) Hu, W.; Xu, X.-F.; Zhou, J.; Liu, W.-J.; Huang, H.-X.; Hu, J.; Yang, L.-P.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782. For review:
(b) Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427. For selected examples:
(c) Terada, M.; Toda, Y. Angew. Chem., Int. Ed. 2012, 51, 2093.
(d) Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nat. Chem. 2012, 4, 733.
(e) Zhang, D.; Qiu, H.; Jiang, L.; Lv, F.; Ma, C.; Hu, W. Angew. Chem., Int. Ed. 2013, 52, 13356.
(f) Jia, S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem., Int. Ed. 2014, 53, 13098.
(g) Jing, C.; Dong, X.; Hu, W. Org. Lett. 2015, 17, 4336.
[17] (a) Chen, D.-F.; Wu, P.-Y.; Gong, L.-Z. Org. Lett. 2013, 15, 3958.
(b) Saito, H.; Iwai, R.; Uchiyama, T.; Miyake, M.; Miyairi, S. Chem. Pharm. Bull. 2010, 58, 872.
[18] Li, M.; Guo, X.; Jin, W.; Zheng, Q.; Liu, S.; Hu, W. Chem. Commun. 2016, 52, 2736.
[19] (a) Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381.
(b) Shen, K.; Liu, X.; Lin, L.; Feng, X. Chem. Sci. 2012, 3, 327.
(c) Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247.
(d) Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023.
(e) Cheng, D.; Ishihara, Y.; Tan, B.; Barbas Ⅲ, C. F. ACS Catal. 2014, 4, 743.
[20] (a) Cao, Z.-Y.; Wang, Y.-H.; Zeng, X.-P.; Zhou, J. Tetrahedron Lett. 2014, 55, 2571. For selected examples, see:
(b) Mei, L.-Y.; Tang, X.-Y.; Shi, M. Chem. Eur. J. 2014, 20, 13136.
(c) Wu, M.-Y.; He, W.-W.; Liu, X.-Y.; Tan, B. Angew. Chem., Int. Ed. 2015, 54, 9409.

[21] (a) Cao, Z.-Y.; Zhou, F.; Zhou, J. Acc. Chem. Res. 2018, 51, 1443. For selected examples, see:
(b) Liu, Y.-L.; Wang, B.-L.; Cao, J.-J.; Chen, L.; Zhang, Y.-X.; Wang, C.; Zhou, J. J. Am. Chem. Soc. 2010, 132, 15176.
(c) Ding, M.; Zhou, F.; Liu, Y.-L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. Chem. Sci. 2011, 2, 2035.
(d) Zhou, F.; Tan, C.; Tang, J.; Zhang, Y.-Y.; Gao, W.-M.; Wu, H.-H.; Yu, Y.-H.; Zhou, J. J. Am. Chem. Soc. 2013, 135, 10994.
(e) Liu, Y.-L.; Wang, X.; Zhao, Y.-L.; Zhu, F.; Zeng, X.-P.; Chen, L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. Angew. Chem., Int. Ed. 2013, 52, 13735.
(f) Yu, J.-S.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L.; Zhou, J. Angew. Chem., Int. Ed. 2015, 54, 7381.
(g) Xu, P.-W.; Liu, J.-K.; Shen, L.; Cao, Z.-Y.; Zhao, X.-L.; Yan, J.; Zhou, J. Nat. Commun. 2017, 8, 1619.
[22] (a) Cao, Z.-Y.; Zhou, F.; Yu, Y.-H.; Zhou, J. Org. Lett. 2013, 15, 42.
(b) Cao, Z.-Y.; Wang, X.; Tan, C.; Zhao, X.-L.; Zhou, J.; Ding, K. J. Am. Chem. Soc. 2013, 135, 8197.
[23] (a) Ren, L.; Lian, X.-L.; Gong, L.-Z. Chem. Eur. J. 2013, 19, 3315.
(b) Chen, D.-F.; Zhao, F.; Hu, Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 10763.
(c) Chen, D.-F.; Zhang, C.-L.; Hu, Y.; Han, Z.-Y.; Gong, L.-Z. Org. Chem. Front. 2015, 2, 956.
[24] (a) Cao, J.-J.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2010, 49, 4976.
(b) Zeng, X.-P.; Cao, Z.-Y.; Wang, X.; Chen, L.; Zhou, F.; Zhu, F.; Wang, C.-H.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 416.
[25] Yin, X.-P.; Zeng, X.-P.; Liu, Y.-L.; Liao, F.-M.; Yu, J.-S.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 13740.
[26] (a) Cao, Z.-Y.; Zhao, Y.-L.; Zhou, J. Chem. Commun. 2016, 52, 2537.
(b) Zhao, Y.-L.; Cao, Z.-Y.; Zeng, X.-P.; Shi, J.-M.; Yu, Y.-H.; Zhou, J. Chem. Commun. 2016, 52, 3943.
[27] Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem., Int. Ed. 2017, 56, 2459.
[28] For selected examples:(a) Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819.
(b) Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.-P.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7200.
(c) Jiang, K.; Jia, Z.-J.; Chen, S.; Wu, L.; Chen, Y.-C. Chem. Eur. J. 2010, 16, 2852.
(d) Tan, B.; Hernández-Torres, G.; Barbas Ⅲ, C.-F. J. Am. Chem. Soc. 2011, 133, 12354.
(e) Yang, W.; Du, D.-M. Chem. Commun. 2013‚ 49, 8842.
(f) Zheng, H.; He, P.; Liu, Y.; Zhang, Y.; Liu, X.; Lin, L.; Feng, X. Chem. Commun. 2014‚ 50, 8794.
(g) Wang, Y.; Tu, M.-S.; Yin, L.; Sun, M.; Shi, F. J. Org. Chem. 2015, 80, 3223.
(h) Zhu, S.; Xu, L.; Wang, L.; Xiao, J. Chin. J. Org. Chem. 2016, 36, 1229(in Chinese). (朱帅, 徐鲁斌, 王亮, 肖建, 有机化学, 2016, 36, 1229.)
[29] (a) Mori, M. Eur. J. Org. Chem. 2007, 4981.
(b) Negishi, E.-I.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474.
(c) Negishi, E.-I.; Wang, G.; Rao, H.; Xu, Z. J. Org. Chem. 2010, 75, 3151.
(d) Manikandan, R.; Jeganmohan, M. Org. Biomol. Chem. 2015, 13, 10420.
(e) Liao, F.; Yu, J.; Zhou, J. Chin. J. Org. Chem. 2017, 37, 2175(in Chinese). (廖富民, 余金生, 周剑, 有机化学, 2017, 37, 2175.)
[30] For our efforts in selective fluoroalkylation using fluorinated enol silyl ethers, see ref. 27 and (a) Liu, Y.-L.; Zhou, J. Chem. Commun. 2012, 48, 1919.
(b) Liu, Y.-L.; Liao, F.-M.; Niu, Y.-F.; Zhao, X.-L.; Zhou, J. Org. Chem. Front. 2014, 1, 742.
(c) Liu, Y.-L.; Zhou, J. Acta Chim. Sinica 2012, 70, 1451(in Chinese). (刘运林, 周剑, 化学学报, 2012, 70, 1451.)
(d) Yu, J.-S.; Liu, Y.-L.; Tang, J.; Wang, X.; Zhou, J. Angew. Chem. Int. Ed. 2014, 53, 9512.
(e) Liao, F.-M.; Liu, Y.-L.; Yu, J.-S.; Zhou, F.; Zhou, J. Org. Biomol. Chem. 2015, 13, 8906.
(f) Yu, J.-S.; Zhou, J. Org. Biomol. Chem. 2015, 13, 10968.
(g) Yu, J.-S.; Zhou, J. Org. Chem. Front. 2016, 3, 298.
(h) Yu, J.-S.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L.; Zhou, J. Angew. Chem. Int. Ed. 2015, 54, 7381.
(i) Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730.
(j) Liao, F.-M.; Gao, X.-T.; Hu, X.-S.; Xie, S.-L.; Yu, J.-S.; Zhou, J. Sci. Bull. 2017, 62, 1504.

Au(I)/手性双功能叔胺催化实现的一锅法串联成烯/不对称环化反应构建螺环季碳氧化吲哚

Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments