碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成

doi:10.6023/cjoc201903050

有机化学 ›› 2019, Vol. 39 ›› Issue (6): 1655-1664.DOI: 10.6023/cjoc201903050 上一篇下一篇

所属专题：金属有机化学；碳氢活化合辑2018-2019

研究论文

碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成

杨云^a, 刘慧慧^a, 刘小兵^a, 刘田田^b, 朱玉芹^b, 张安安^b, 王涛^b, 华远照^c, 王敏灿^c, 毛国梁^a, 刘澜涛^b,c

a 东北石油大学化学化工学院大庆 163318;
b 商丘师范学院化学化工学院商丘 476000;
c 郑州大学化学与分子工程学院郑州 450001

收稿日期:2019-03-24 修回日期:2019-05-10 发布日期:2019-05-15
通讯作者: 毛国梁, 刘澜涛 E-mail:liult05@iccas.ac.cn;maoguoliang@nepu.edu.cn
基金资助:
国家自然科学基金（No.21572126）、河南省高校科技创新人才基金（No.14HASTIT016）、河南省科技创新杰出人才（No.2018JQ0011）资助项目.

Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination

Yang Yun^a, Liu Huihui^a, Liu Xiaobing^a, Liu Tiantian^b, Zhu Yuqin^b, Zhang Anan^b, Wang Tao^b, Hua Yuanzhao^c, Wang Mincan^c, Mao Guoliang^a, Liu Lantao^b,c

a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318;
b College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000;
c College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received:2019-03-24 Revised:2019-05-10 Published:2019-05-15
Contact: 10.6023/cjoc201903050 E-mail:liult05@iccas.ac.cn;maoguoliang@nepu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011).

文章分享

1. 碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成.PDF(4816KB)

摘要/Abstract

由于较低的旋转能垒，轴手性烯基芳烃衍生物的催化不对称合成存在很大挑战.氧化吲哚是天然产物的重要骨架，也是生物活性分子及药物的重要合成子.作者通过碳钯化/C-H键的烯基化串联反应实现了含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成.（4R，5R）-2，2-二甲基-α，α，α'，α'-四苯基-1，3-二氧戊环-4，5-二甲醇（TADDOL）衍生的亚膦酰胺配体给出了较好的产率和中等的对映选择性.产物在110℃加热10 h后ee值没有降低，表明其手性轴具有很好的热稳定性.

关键词: 不对称合成, 轴手性, 烯基芳烃, 碳钯化, C-H键烯基化, 氧化吲哚

Due to the lower configuration stability of vinylarenes, arsing from the relatively lower rotational barriers, their catalytic asymmetric synthesis remains a daunting task. Oxindoles moiety are privileged framework of natural products and building blocks of bioactive molecules as well as pharmaceuticals. The asymmetric synthesis of axial chiral vinylarenes fearturing oxindole moiety via sequential carbopalladation/C-H olefination from readily available materials with palladium catalysis has been developed. (4R,5R)-(-)-2,2-Dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL)-derived phosphoramidite gave products with good yield and moderate ee value. The erosion of optical purity was not observed even after heating the product for 10 h at 110℃, which indicates the excellent stability of the chiral axial.

Key words: asymmetric synthesis, axial chirality, vinyl-arenes, carbopalladation, C-H olefination, oxindole

引用此文

杨云, 刘慧慧, 刘小兵, 刘田田, 朱玉芹, 张安安, 王涛, 华远照, 王敏灿, 毛国梁, 刘澜涛. 碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成[J]. 有机化学, 2019, 39(6): 1655-1664.

Yang Yun, Liu Huihui, Liu Xiaobing, Liu Tiantian, Zhu Yuqin, Zhang Anan, Wang Tao, Hua Yuanzhao, Wang Mincan, Mao Guoliang, Liu Lantao. Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination[J]. Chin. J. Org. Chem., 2019, 39(6): 1655-1664.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Bringmann, G.; Menche, D. Acc. Chem. Res. 2001, 34, 615.
(b) Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563.
[2] (a) LaPlante, S. R.; Edwards, P. J.; Fader, L. D.; Jakalian, A.; Hucke, O. ChemMedChem 2011, 6, 505.
(b) Clayden, J.; Moran, W. J.; Edwards, P. J.; S. LaPlante, R. Angew. Chem., Int. Ed. 2009, 48, 6398.
(c) Glunz, P. W. Bioorg. Med. Chem. Lett. 2018, 28, 53.
[3] (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
(b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
(c) Kocovský, P.; Vyskocil, Š.; Smrcina, M. Chem. Rev. 2003, 103, 3213.
(d) Akiyama, T. Chem. Rev. 2007, 107, 5744.
[4] For selected reviews, see:(a) Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
(b) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193.
(c) Quinonero, O.; Bressy, C.; Bugaut, X. Angew. Chem., Int. Ed. 2014, 53, 10861.
(d) Zhang, D.; Wang, Q. Coord. Chem. Rev. 2015, 286, 1.
(e) Wencel-Delord, J.; Panossian, A.; Leroux, F. R.; Colobert, F. Chem. Soc. Rev. 2015, 44, 3418.
(f) Loxq, P.; Manoury, E.; Poli, R.; Deydier, E.; Labande, A. Coord. Chem. Rev. 2016, 308, 131.
(g) Wang, Y.-B.; Tan, B. Acc. Chem. Res. 2018, 51, 534.
(h) Zilate, B.; Castrogiovanni, A.; Sparr, C. ACS Catal. 2018, 8, 2981.
[5] Tanaka, K.; Shibata, T. In Transition-Metal-Mediated Aromatic Ring Construction, Ed.:Tanaka, K., John Wiley & Sons, Inc., Hoboken, New Jersey, 2013, pp. 255~279.
[6] (a) Baker, R. W.; Hambley, T. W.; Turner, P.; Wallace, B. J. Chem. Commun. 1996, 2571.
(b)Hattori, T.; Date, M.; Sakurai, K.; Morohashi, N.; Kosugi, H.; Miyano, S. Tetrahedron Lett. 2001, 42, 8035.
[7] (a) Feng, J.; Li, B.; He, Y.; Gu, Z. Angew. Chem., Int. Ed. 2016, 55, 2186.
(b) Feng, J.; Li, B.; Jiang, J.; Zhang, M.; Ouyang, W.; Li, C.; Fu, Y.; Gu, Z. Chin. J. Chem. 2018, 36, 11.
[8] Jolliffe, J. D.; Armstrong, R. J.; Smith, M. D. Nat. Chem. 2017, 9, 558.
[9] Zheng, S.-C.; Wu, S.; Zhou, Q.; Chung, L. W.; Ye, L.; Tan, B. Nat. Commun. 2017, 8, 15238.
[10] Jia, S. Q.; Chen, Z. L.; Zhang, N.; Tan, Y.; Liu, Y. D.; Deng, J.; Yan, H. L. J. Am. Chem. Soc. 2018, 140, 7056.
[11] For selected reviews, see:
(a) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
(b) Wencel-Delord, J.; Colobert, F. Chem.-Eur. J. 2013, 19, 14010.
(c) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
(d) You, S.-L. Asymmetric Functionalization of C-H Bonds, RSC, Cambridge, U. K., 2015.
(e) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908.
(f) Gao, D.-W.; Gu, Q.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2017, 50, 351.
(f) Huang, J.; Gu, Q.; You, S.-L. Chin. J. Org. Chem. 2018, 38, 51 (in Chinese).(黄家翩, 顾庆, 游书力, 有机化学, 2018, 38, 51.)
(g) Wang, Y.; Zhang, A.; Liu, L.; Kang, J.; Zhang, F.; Ma, W. Chin. J. Org. Chem. 2015, 35, 1399 (in Chinese).(王艳芳, 张安安, 刘澜涛, 康建勋, 张富强, 马文瑾, 有机化学, 2015, 35, 1399.)
[12] Pd-catalyzed:(a) Li, S.-X.; Ma, Y.-N.; Yang, S.-D. Org. Lett. 2017, 19, 842.
(b) He, C.; Hou, M.; Zhu, Z.; Gu, Z. ACS Catal. 2017, 7, 5316.
(c) Yao, Q.-J.; Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem., Int. Ed. 2017, 56, 6617.
(d) Liao, G.; Yao, Q.-J.; Zhang, Z.-Z.; Wu, Y.-J.; Huang, D.-Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 3665.
(e) Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956.
Rh-catalyzed:
(f) Kakiuchi, F.; Gendre, P. Le; Yamada, A.; Ohtaki, H.; Murai, S. Tetrahedron:Asymmetry 2000, 11, 2647.
(g) Zheng, J.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 13244.
(h) Zheng, J.; Cui, W.-J.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 5242.
[13] Pd-catalyzed:(a) Yamaguchi, K.; Yamaguchi, J.; Studer, A.; Itami, K. Chem. Sci. 2012, 3, 2165.
(b) Yamaguchi, K.; Kondo, H.; Yamaguchi, J.; Itami, K. Chem. Sci. 2013, 4, 3753.
(c) Nishimoto, Y.; Kondo, H.; Yamaguchi, K.; Yokogawa, D.; Yamaguchi, J.; Itami, K.; Irle, S. J. Org. Chem. 2017, 82, 4900.
(d) Newton, C. G.; Jennifer Kuziola, E. B.; Wodrich, M. D.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 11040.
Rh-catalyzed:(e) Jia, Z.-J.; Merten, C.; Gontla, R.; Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2017, 56, 2429.
(f) Shibuya, T.; Shibata, Y.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 3963.
[14] (a) Sasaki, E.; Miyoshi, K.; Nozawa, Y.; Kanda, A.; Nakano, K.; Yamasaki, Y.; Miyake, H.; Matsuura, N. Pharmacology 2001, 63, 17.
(b) Yu, L.-F.; Li, Y.-Y.; Su, M.-B.; Zhang, M.; Zhang, W.; Zhang, L.-N.; Pang, T.; Zhang, R.-T.; Liu, B.; Li, J.-Y.; Li, J.; Nan, F.-J. ACS Med. Chem. Lett. 2013, 4, 475.
(c) Pal, A.; Ganguly, A.; Ghosh, A.; Yousuf, M.; Rathore, B.; Banerjee, R.; Adhikari, S. ChemMedChem 2014, 9, 727.
[15] (a) Liu, L.; Zhang, A.-A.; Zhao, R.-J.; Li, F.; Meng, T.-J.; Ishida, N.; Murakami, M.; Zhao, W.-X. Org. Lett. 2014, 16, 5336.
(b) Liu, L.; Zhang, A.-A.; Wang, Y.; Zhang, F.; Zuo, Z.; Zhao, W.-X.; Feng, C.-L.; Ma, W. Org. Lett. 2015, 17, 2046.
[16] Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. P. Org. Lett. 2006, 8, 4927.
[17] Zhou, Y.; Zhang, X.; Zhang, Y.; Ruan, L.; Zhang, J.; Zhangnegrerie, D.; Du, Y. Org. Lett. 2017, 19, 150.

碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成

Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	陈宛婷, 钟雄威, 邢佳乐, 吴昌书, 高杨. C—N轴手性化合物的不对称催化合成研究进展[J]. 有机化学, 2024, 44(2): 349-377.
[2]	姜权彬. 经由氮杂邻联烯醌中间体合成轴手性化合物的研究进展[J]. 有机化学, 2024, 44(1): 159-172.
[3]	王化坤, 任晓龙, 宣宜宁. 卤盐催化的α,β-环氧羧酸酯与异氰酸酯[3＋2]环加成反应研究[J]. 有机化学, 2024, 44(1): 251-258.
[4]	于士航, 刘嘉威, 安碧玉, 边庆花, 王敏, 钟江春. 黑腹尼虎天牛接触性信息素的不对称合成[J]. 有机化学, 2024, 44(1): 301-308.
[5]	岁丹丹, 岑南楠, 龚若蕖, 陈阳, 陈文博. 无支持电解质条件下连续流电化学合成三氟甲基化氧化吲哚[J]. 有机化学, 2023, 43(9): 3239-3245.
[6]	王玉超, 刘晋彪, 何智涛. 钯催化共轭二烯的不对称氢官能团化[J]. 有机化学, 2023, 43(8): 2614-2627.
[7]	宋亭谕, 李冉, 黄利华, 贾世琨, 梅光建. N—N单键阻转异构体的催化不对称合成[J]. 有机化学, 2023, 43(6): 1977-1990.
[8]	罗诚, 尹艳丽, 江智勇. P-手性膦氧化物的不对称合成研究进展[J]. 有机化学, 2023, 43(6): 1963-1976.
[9]	蒙玲, 汪君. 硫代黄烷酮类衍生物的合成研究进展[J]. 有机化学, 2023, 43(3): 873-891.
[10]	张怀远, 许诺, 唐蓉萍, 石星丽. 手性高价碘试剂诱导的不对称去芳构化反应研究进展[J]. 有机化学, 2023, 43(11): 3784-3805.
[11]	匡鑫, 丁昌华, 吴奕晨, 王鹏. 手性烯丙基硅烷的催化对映选择性合成[J]. 有机化学, 2023, 43(10): 3367-3387.
[12]	濮留洋, 李芷悦, 李利民, 马玉翠, 马民, 胡胜全, 吴正治. 秋水仙碱及其天然类似物(–)-N-乙酰秋水酚甲醚的不对称合成[J]. 有机化学, 2023, 43(1): 313-319.
[13]	赵薇, 刘京, 何向奎, 蒋豪, 陆良秋, 肖文精. 氮杂环卡宾(NHC)催化的联芳基二醛去对称化构建轴手性醛类化合物[J]. 有机化学, 2022, 42(8): 2504-2514.
[14]	毛沅浩, 高延峰, 苗志伟. 过渡金属催化不对称环化反应合成七元环化合物研究进展[J]. 有机化学, 2022, 42(7): 1904-1924.
[15]	姚婷, 李佳燕, 王佳明, 赵常贵. 氮杂环卡宾催化构筑含七元环结构的研究进展[J]. 有机化学, 2022, 42(4): 925-944.