有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应

doi:10.6023/cjoc202112023

有机化学 ›› 2022, Vol. 42 ›› Issue (6): 1722-1734.DOI: 10.6023/cjoc202112023 上一篇下一篇

研究论文

有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应

王兴^a, 宋倩倩^a, 陈续玲^b, 李鹏飞^b^,^*(), 齐昀坤^a^,^*(), 李文军^a^,^*()

a 青岛大学药学院山东青岛 266073
b 南方科技大学理学院格拉布斯研究院化学系广东省催化化学重点实验室广东深圳 518055

收稿日期:2021-12-18 修回日期:2022-02-28 发布日期:2022-03-08
通讯作者: 李鹏飞, 齐昀坤, 李文军
作者简介:
† 共同第一作者
基金资助:
山东省自然科学基金(ZR2021MB026); 山东省泰山学者(tsqn201812047); 深圳市科委创新(20200925151614002); 广东省催化化学重点实验室(2020B121201002)

Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

Xing Wang^a, Qianqian Song^a, Xuling Chen^b, Pengfei Li^b(), Yunkun Qi^a(), Wenjun Li^a()

a School of Pharmacy, Qingdao University, Qingdao, Shandong 266073
b Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, South University of Science and Technology of China, Shenzhen, Guangzhou 518055

Received:2021-12-18 Revised:2022-02-28 Published:2022-03-08
Contact: Pengfei Li, Yunkun Qi, Wenjun Li
About author:
† These authors contributed equally to this work
Supported by:
Natural Science Foundation of Shandong Province(ZR2021MB026); Special Funds of the Taishan Scholar Program of Shandong Province(tsqn201812047); Shenzhen Innovation of Science and Technology Commission(20200925151614002); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

文章分享

1. 221722S.pdf(4731KB)

摘要/Abstract

报道了在手性磷酸作用下6-吲哚甲醇原位生成6-亚甲基-6H-吲哚, 继而与异噁唑-5(4H)-酮发生不对称1,8-共轭加成反应. 该反应实现了异噁唑-5(4H)-酮的对映选择性N-烷基化, 以70%~83%的产率和61%~96%的对映选择性得到共轭加成产物.

关键词: 不对称有机催化, 共轭加成, 异噁唑-5(4H)-酮, 6-亚甲基-6H-吲哚

A chiral phosphoric acid catalyzed aza-1,8-conjugate addition of isoxazol-5(4H)-ones to 6-methylene-6H-indoles formed in situ from 6-indolylmethanols has been developed for the first time. Notably, the remote stereocontrolled 1,8-addition of isoxazol-5(4H)-ones was featured by N-selectivity, affording aza-adducts in 70%~83% yields with 61%~96% ee.

Key words: asymmetric organocatalysis, conjugate addition, isoxazol-5(4H)-ones, 6-methylene-6H-indole

引用此文

王兴, 宋倩倩, 陈续玲, 李鹏飞, 齐昀坤, 李文军. 有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应[J]. 有机化学, 2022, 42(6): 1722-1734.

Xing Wang, Qianqian Song, Xuling Chen, Pengfei Li, Yunkun Qi, Wenjun Li. Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1722-1734.

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

分享此文

图/表 6

参考文献 25

[5]	Beccalli, E. M.; Marchesini, A. Synthesis 1991, 861.
[6]	(a) Okamoto, K.; Oda, T.; Kohigashi, S.; Ohe, K. Angew. Chem., Int. Ed. 2011, 50, 11470. doi: 10.1002/anie.201105153 pmid: 28832162
	(b) Okamoto, K.; Shimbayashi, T.; Yoshida, M.; Nanya, A.; Ohe, K. Angew. Chem., Int. Ed. 2016, 55, 7199. doi: 10.1002/anie.201602241 pmid: 28832162
	(c) Rieckhoff, S.; Titze, M.; Frey, W.; Peters, R. Org. Lett. 2017, 19, 4436. doi: 10.1021/acs.orglett.7b01895 pmid: 28832162
[7]	Okamoto, K.; Shimbayashi, T.; Tamura, E.; Ohe, K. Chem. Eur. J. 2014, 20, 1490. doi: 10.1002/chem.201304211
[8]	(a) Rieckhoff, S.; Hellmuth, T.; Peters, R. J. Org. Chem. 2015, 80, 6822. doi: 10.1021/acs.joc.5b01065 pmid: 26101943
	(b) Fernandes, A. A. G.; Stivanin, M. L.; Jurberg, I. D. ChemistrySelect 2019, 4, 3360. doi: 10.1002/slct.201900761 pmid: 26101943
[9]	Rieckhoff, S.; Frey, W.; Peters, R. Eur. J. Org. Chem. 2018, 1797.
[10]	(a) Liang, H.-W.; Yang, Z.; Jiang, K.; Ye, J.; Wei, Y. Angew. Chem., Int. Ed. 2018, 57, 5720. doi: 10.1002/anie.201801363
	(b) Lang, J.; Wei, Y. Synlett 2019, 30, 252. doi: 10.1055/s-0037-1610348
[11]	(a) Zhao, T.; Zhang, H.; Cui, L.; Wang, C.; Qu, J.; Wang, B. ChemistrySelect 2016, 1, 3713. doi: 10.1002/slct.201600823 pmid: 32182085
	(b) Shimbayashi, T.; Matsushita, G.; Nanya, A.; Eguchi, A.; Okamoto, K.; Ohe, K. ACS Catal. 2018, 8, 7773. doi: 10.1021/acscatal.8b01646 pmid: 32182085
	(c) Christodoulou, M. S.; Giofrè, S.; Beccalli, E. M.; Foschi, F.; Broggini, G. Org. Lett. 2020, 22, 2735. doi: 10.1021/acs.orglett.0c00709 pmid: 32182085
	(d) Wang, T.; Pi, C.; Wu, Y.; Cui, X. Org. Lett. 2020, 22, 6484. doi: 10.1021/acs.orglett.0c02283 pmid: 32182085
[12]	(a) Meng, W.-T.; Zheng, Y.; Nie, J.; Xiong, H.-Y.; Ma, J.-A. J. Org. Chem. 2013, 78, 559. doi: 10.1021/jo302419e pmid: 29240444
	(b) Hellmuth, T.; Frey, W.; Peters, R. Angew. Chem., Int. Ed. 2015, 54, 2788. doi: 10.1002/anie.201410933 pmid: 29240444
	(c) Zhang, H.; Wang, B.; Cui, L.; Bao, X.; Qu, J.; Song, Y. Eur. J. Org. Chem. 2015, 2143. pmid: 29240444
	(d) Rieckhoff, S.; Meisner, J.; Kästner, J.; Frey, W.; Peters, R. Angew. Chem., Int. Ed. 2018, 57, 1404. doi: 10.1002/anie.201710940 pmid: 29240444
	(e) Xiao, W.; Zhou, Z.; Yang, Q.-Q.; Du, W.; Chen, Y.-C. Adv. Synth. Catal. 2018, 360, 3526. doi: 10.1002/adsc.201800636 pmid: 29240444
	(f) Xiao, W.; Yang, Q.-Q.; Chen, Z.; Ouyang, Q.; Du, W.; Chen, Y.-C. Org. Lett. 2018, 20, 236. doi: 10.1021/acs.orglett.7b03598 pmid: 29240444
[13]	Torán, R.; Vila, C.; Sanz-Marco, A.; Muñoz, M. C.; Pedro, J. R.; Blay, G. Eur. J. Org. Chem. 2020, 627.
[14]	Qi, S.-S.; Jiang, Z.-H.; Chu, M.-M.; Wang, Y.-F.; Chen, X.-Y.; Ju, W.-Z.; Xu, D.-Q. Org. Biomol. Chem. 2020, 18, 2398. doi: 10.1039/D0OB00393J
[15]	For selected reviews, see: (b) Fuson, R. C. Chem. Rev. 1935, 16, 1. doi: 10.1021/cr60053a001
	(b) Jiang, H.; Albrecht, Ł.; Jørgenson, K. A. Chem. Sci. 2013, 4, 2287. doi: 10.1039/c3sc50405k
	(c) Curti, C.; Battistini, L.; Sartori, A.; Zanardi, F. Chem. Rev. 2020, 120, 2448. doi: 10.1021/acs.chemrev.9b00481
[16]	Uraguchi, D.; Yoshioka, K.; Ueki, Y.; Ooi, T. J. Am. Chem. Soc. 2012, 134, 19370. doi: 10.1021/ja310209g pmid: 23145913
[17]	(a) Qian, D.; Wu, L.; Lin, Z.; Sun, J. Nat. Commun. 2017, 8, 567. doi: 10.1038/s41467-017-00251-x pmid: 31544464
	(b) Chen, M.; Qian, D.; Sun, J. Org. Lett. 2019, 21, 8127. doi: 10.1021/acs.orglett.9b03224 pmid: 31544464
[18]	Liu, X.; Zhang, J.; Bai, L.; Wang, L.; Yang, D.; Wang, R. Chem. Sci. 2020, 11, 671. doi: 10.1039/C9SC05320D
[19]	(a) Zhang, P.; Huang, Q.; Cheng, Y.; Li, R.; Li, P.; Li, W. Org. Lett. 2019, 21, 503. doi: 10.1021/acs.orglett.8b03801 pmid: 31486650
	(b) Zhang, L.; Han, Y.; Huang, A.; Zhang, P.; Li, P.; Li, W. Org. Lett. 2019, 21, 7415. doi: 10.1021/acs.orglett.9b02726 pmid: 31486650
[20]	Yue, C.; Na, F.; Fang, X.; Cao, Y.; Antilla, J. C. Angew. Chem., Int. Ed. 2018, 57, 11004. doi: 10.1002/anie.201804330
[21]	Li, X.; Sun, J. Angew. Chem., Int. Ed. 2020, 59, 17049. doi: 10.1002/anie.202006137
[22]	(a) Li, W.; Xu, X.; Liu, Y.; Gao, H.; Cheng, Y.; Li, P. Org. Lett. 2018, 20, 1142. doi: 10.1021/acs.orglett.8b00072
[1]	da Silva, A. F.; Fernandes, A. A. G.; Thurow, S.; Stivanin, M. L.; Jurberg, I. D. Synthesis 2018, 50, 2473. doi: 10.1055/s-0036-1589534
[2]	(a) Beccalli, E. M.; Rosa, C. L.; Marchesini, A. J. Org. Chem. 1984, 49, 4287. doi: 10.1021/jo00196a034 pmid: 28892631
	(b) Jurberg, I. D.; Davies, H. M. L. Org. Lett. 2017, 19, 5158. doi: 10.1021/acs.orglett.7b02436 pmid: 28892631
	(c) Zhu, Y.-M.; Zhang, W.; Li, H.; Xu, X.-P.; Ji, S.-J. Adv. Synth. Catal. 2021, 363, 808. doi: 10.1002/adsc.202001200 pmid: 28892631
[3]	(a) Boivin, J.; Elkaim, L.; Ferro, P. G.; Zard, S. Z. Tetrahedron Lett. 1991, 32, 5321. doi: 10.1016/S0040-4039(00)92375-X
	(b) Boivin, J.; Huppé, S.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 8735. doi: 10.1016/S0040-4039(96)02015-1
	(c) Boutillier, P.; Zard, S. Z. Chem. Commun. 2001, 1304.
[4]	Beccalli, E. M.; Marchesini, A.; Pilati, T. Synthesis 1991, 127.
[22]	(b) Li, W.; Yuan, H.; Liu, Z.; Zhang, Z.; Cheng, Y.; Li, P. Adv. Synth. Catal. 2018, 360, 2460. doi: 10.1002/adsc.201800337
	(c) Li, F.; Chen, X.; Liang, S.; Shi, Z.; Li, P.; Li, W. Org. Chem. Front. 2020, 7, 3446. doi: 10.1039/D0QO00888E
	(d) Song, Q.; Zhang, P.; Liang, S.; Chen, X.; Li, P.; Li, W. Org. Lett. 2020, 22, 7859. doi: 10.1021/acs.orglett.0c02769
[23]	(a) Li, P.; Fang, F.; Chen, J.; Wang, J. Tetrahedron: Asymmetry 2014, 25, 98. pmid: 31486458
	(b) Fang, F.; Hua, G.; Shi, F.; Li, P. Org. Biomol. Chem. 2015, 13, 4395. doi: 10.1039/c5ob00175g pmid: 31486458
	(c) Huang, Q.; Zhang, L.; Cheng, Y.; Li, P.; Li, W. Adv. Synth. Catal. 2018, 360, 3266. doi: 10.1002/adsc.201800642 pmid: 31486458
	(d) Huang, Q.; Cheng, Y.; Yuan, H.; Chang, X.; Li, P.; Li, W. Org. Chem. Front. 2018, 5, 3226. doi: 10.1039/C8QO00814K pmid: 31486458
	(e) Qian, C.; Zhang, P.; Li, W.; Li, P. Asian J. Org. Chem. 2019, 8, 242. pmid: 31486458
	(f) Zhang, C.; Shang, X.; Cheng, Y.; Li, F.; Zhao, H.; Li, P.; Li, W. Org. Biomol. Chem. 2019, 17, 8374. doi: 10.1039/c9ob01870k pmid: 31486458
	(g) Li, F.; Yang, Z.; Yang, Y.; Huang, Q.; Chen, X.; Li, P.; Dong, M.; Li, W. Adv. Synth. Catal. 2021, 363, 2557. doi: 10.1002/adsc.202100039 pmid: 31486458
[24]	For selected recent reviews, see: (a) Zhang Y.-C.; Jiang, F.; Shi, F. Acc. Chem. Res. 2020, 53, 425. doi: 10.1021/acs.accounts.9b00549 pmid: 32720968
	(b) Zeng, L.; Lin, Y.; Cui, S. Chem. Asian J. 2020, 15, 973. doi: 10.1002/asia.201901806 pmid: 32720968
	(c) Pradhan, S.; De, P. B.; Shah, T. A.; Punniyamurthy, T. Chem. Asian J. 2020, 15, 4184. doi: 10.1002/asia.202001159 pmid: 32720968
	(d) Li, T.-Z.; Liu, S.-J.; Tan, W.; Shi, F. Chem. Eur. J. 2020, 26, 15779. doi: 10.1002/chem.202001397 pmid: 32720968
	(e) Cerveri, A.; Bandini, M. Chin. J. Chem. 2020, 38, 287. doi: 10.1002/cjoc.201900446 pmid: 32720968
	(f) Alonso, J. M.; Muñoz, M. P. Eur. J. Org. Chem. 2020, 7197. pmid: 32720968
	(g) Milcendeau, P.; Sabat, N.; Ferry, A.; Guinchard, X. Org. Biomol. Chem. 2020, 18, 6006. doi: 10.1039/d0ob01245a pmid: 32720968
	(h) Bonandi, E.; Perdicchia, D.; Colombo, E.; Foschi, F.; Marzullo, P.; Passarella, D. Org. Biomol. Chem. 2020, 18, 6211. doi: 10.1039/d0ob01094d pmid: 32720968
	(i) Sheng, F.-T.; Wang, J.-Y.; Tan, W.; Zhang, Y.-C.; Shi, F. Org. Chem. Front. 2020, 7, 3967. doi: 10.1039/D0QO01124J pmid: 32720968
	(j) Deka, B.; Deb, M. L.; Baruah, P. K. Topics Curr. Chem. 2020, 378, 22. doi: 10.1007/s41061-020-0287-7 pmid: 32720968
	(k) Neto, J.; Zeni, G. Org. Chem. Front. 2020, 7, 155. doi: 10.1039/C9QO01315F pmid: 32720968
	(l) Tu, M.; Chen, K.; Wu, P.; Zhang, Y.; Liu, X.; Shi, F. Org. Chem. Front. 2021, 8, 2643. doi: 10.1039/D0QO01643H pmid: 32720968
[25]	For selected reviews on CPAs, see: (a) Akiyama, T. Chem. Rev. 2007, 107, 5744. doi: 10.1021/cr068374j pmid: 25203602
	(b) Terada, M. Synthesis 2010, 12, 1929. pmid: 25203602
	(c) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156. doi: 10.1021/ar2000343 pmid: 25203602
	(d) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047. doi: 10.1021/cr5001496 pmid: 25203602
	(e) Wu, H.; He, Y.-P.; Shi, F. Synthesis 2015, 47, 1990. doi: 10.1055/s-0034-1378837 pmid: 25203602
	(f) Merad, J.; Lalli, C.; Bernadat, G.; Maury, J.; Masson, G. Chem. Eur. J. 2018, 24, 3925. pmid: 25203602

Entry	Catalyst	Solvent	Yield^b/%	ee^c/%
1	CPA-1	CH₂Cl₂	3aa, 75	≈28
2	CPA-2	CH₂Cl₂	3aa, 74	≈53
3	CPA-3	CH₂Cl₂	3aa, 62	≈66
4	CPA-4	CH₂Cl₂	3aa, 57	≈68
5	CPA-5	CH₂Cl₂	3aa, 77	88
6	CPA-6	CH₂Cl₂	3aa, 49	48
7	CPA-5	CHCl₃	3aa, 80	68
8	CPA-5	THF	3aa, 68	43
9	CPA-5	Et₂O	3aa, 65	49
10	CPA-5	Toluene	3aa, 77	76
11	CPA-5	PhCF₃	3aa, 69	90
12	CPA-5	Xylenes	3aa, 70	96
13^d	CPA-5	Xylenes	3aa, 81	96
14^e	CPA-5	Xylenes	3aa, 74	92
15^f	CPA-5	Xylenes	3aa, 83	94

Entry	Catalyst	Solvent	Yield^b/%	ee^c/%
1	CPA-1	CH₂Cl₂	3aa, 75	≈28
2	CPA-2	CH₂Cl₂	3aa, 74	≈53
3	CPA-3	CH₂Cl₂	3aa, 62	≈66
4	CPA-4	CH₂Cl₂	3aa, 57	≈68
5	CPA-5	CH₂Cl₂	3aa, 77	88
6	CPA-6	CH₂Cl₂	3aa, 49	48
7	CPA-5	CHCl₃	3aa, 80	68
8	CPA-5	THF	3aa, 68	43
9	CPA-5	Et₂O	3aa, 65	49
10	CPA-5	Toluene	3aa, 77	76
11	CPA-5	PhCF₃	3aa, 69	90
12	CPA-5	Xylenes	3aa, 70	96
13^d	CPA-5	Xylenes	3aa, 81	96
14^e	CPA-5	Xylenes	3aa, 74	92
15^f	CPA-5	Xylenes	3aa, 83	94

Entry^a	Ar	R¹	Yield^b/%	ee^c/%
1	4-MeOC₄H₆	Ph	3aa, 81	96
2^d	4-MeC₄H₆	Ph	3ba, 76	96
3	4-FC₄H₆	Ph	3ca, 77	96
4	3-MeOC₄H₆	Ph	3da, 70	80
5	3-ClC₄H₆	Ph	3ea, 70	84
6	2-MeC₄H₆	Ph	3fa, 79	67
7^d	Ph	Ph	3ga, 75	77
8	4-MeOC₄H₆	4-MeOC₄H₆	3ha, 81	94
9	4-MeOC₄H₆	2-MeOC₄H₆	3ia, 81	92
10	4-MeOC₄H₆	2-Naphthyl	3ja, 74	95
11	4-MeOC₄H₆	H	3ka, 70	75
12	4-MeOC₄H₆	Me	3la, 79	65

Entry^a	Ar	R¹	Yield^b/%	ee^c/%
1	4-MeOC₄H₆	Ph	3aa, 81	96
2^d	4-MeC₄H₆	Ph	3ba, 76	96
3	4-FC₄H₆	Ph	3ca, 77	96
4	3-MeOC₄H₆	Ph	3da, 70	80
5	3-ClC₄H₆	Ph	3ea, 70	84
6	2-MeC₄H₆	Ph	3fa, 79	67
7^d	Ph	Ph	3ga, 75	77
8	4-MeOC₄H₆	4-MeOC₄H₆	3ha, 81	94
9	4-MeOC₄H₆	2-MeOC₄H₆	3ia, 81	92
10	4-MeOC₄H₆	2-Naphthyl	3ja, 74	95
11	4-MeOC₄H₆	H	3ka, 70	75
12	4-MeOC₄H₆	Me	3la, 79	65

有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应

Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 6

参考文献 25

相关文章 15

编辑推荐

相关统计

本文评价

Entry^a	R²	R³	3, Yield^b/%	ee^c/%
1	Ph	4-MeOC₄H₆	3ab, 82	92
2	Ph	4-ClC₄H₆	3ac, 70	89
3	Ph	4-BrC₄H₆	3ad, 79	94
4	Ph	4-NO₂C₄H₆	3ae, 74	90
5	Ph	3-MeC₄H₆	3af, 79	96
6	Ph	3-ClC₄H₆	3ag, 79	92
7	Ph	3-BrC₄H₆	3ah, 79	96
8	Ph	2-MeC₄H₆	3ai, 77	94
9	Ph	2-BrC₄H₆	3aj, 77	86
10	Ph	2-Naphthyl	3ak, 83	90
11	Ph	1-Naphthyl	3al, 79	96
12	Ph	2-Furyl	3am, 80	66
13^d	Ph	H	3an, 75	63
14	Me	Ph	3ao, 81	61
15^e	Et	Ph	3ap, 72	70
16	Ph	Ph	3aq, 82	84

[1]	陈文龙, 李慧敏, 杨鹏飞, 郑东程, 杨高升. 2-芳甲酰基甲亚基丙二酸酯与Corey叶立德的反应[J]. 有机化学, 2023, 43(4): 1472-1482.
[2]	王东琳, 阚玲珑, 马玉道, 刘磊. 叔丁醇钠催化的δ-腈基-δ-芳基-双取代的对亚甲基苯醌和二芳基氧磷的磷氢化反应研究[J]. 有机化学, 2021, 41(8): 3192-3203.
[3]	李华, 庞靖祥, 刘华铮, 赵长印, 李松, 王恒山, 刘希功. Sc(OTf)₃催化的δ-三氟甲基-δ-芳基-双取代对亚甲基苯醌和硫醇的反应: 高效合成二芳基甲烷硫醚化合物[J]. 有机化学, 2021, 41(8): 3134-3143.
[4]	张同飞, 陈逸波, 高振博. 三氟甲磺酸铜(II)催化的硫醇对烯酮的共轭加成反应[J]. 有机化学, 2021, 41(6): 2424-2434.
[5]	余述燕, 高丽宏, 兰宏兵, 钱恒玉, 尹志刚, 商永嘉. 橙酮衍生氮杂二烯的化学反应进展[J]. 有机化学, 2020, 40(9): 2714-2724.
[6]	王琳, 王楠, 齐越, 孙书涛, 刘希功, 李伟, 刘磊. 基于δ-腈基取代对亚甲基苯醌1,6-氮杂共轭加成的大位阻α-氰胺合成研究[J]. 有机化学, 2020, 40(11): 3934-3943.
[7]	林晔, 杜大明. 方酰胺催化的不对称串联反应合成螺环氧吲哚衍生物研究进展[J]. 有机化学, 2020, 40(10): 3214-3236.
[8]	刘腾, 刘建军, 贺池先, 成飞翔. 多共轭硝基二烯炔/硝基烯炔的合成以及应用研究进展[J]. 有机化学, 2017, 37(10): 2609-2618.
[9]	陈学伟, 辛玉娟, 刘青, 兰支利. 含辅助基的双功能(硫)脲催化剂在不对称有机催化中的应用[J]. 有机化学, 2016, 36(2): 306-314.
[10]	邢爱萍, 田密, 王来来. C₃对称的新型单齿亚磷酸酯配体在不对称氢甲酰化和1,4-共轭加成中的应用研究[J]. 有机化学, 2016, 36(12): 2912-2919.
[11]	唐凤翔, 叶久勇. 铜催化格氏试剂不对称共轭加成研究进展[J]. 有机化学, 2015, 35(7): 1414-1427.
[12]	林敬, 程宇, 康泰然, 何龙, 刘全忠. 不饱和酮亚胺叶立德的分子内共轭加成[J]. 有机化学, 2014, 34(4): 735-740.
[13]	倪承燕, 李文科, 何龙, 刘全忠, 康泰然. 二乙基锌对原位产生吲哚亚胺的对映选择性加成反应[J]. 有机化学, 2012, 32(12): 2322-2327.
[14]	徐涛, 贡卫涛, 叶俊伟, 宁桂玲, 林源. 2,4,6-三苯基吡喃盐与三烷基(芳基)膦的新型共轭加成反应[J]. 有机化学, 2011, 31(10): 1707-1709.
[15]	于艳飞姜岚李争宁单凤军. 铜-手性氮杂环卡宾化合物催化的不对称1,4-共轭加成反应[J]. 有机化学, 2011, 31(04): 443-452.