具有紧密手性环境的联菲酚骨架磷酸的合成

doi:10.6023/cjoc202203019

摘要/Abstract

以轴手性的1,1'-联-2-萘酚(BINOL)和1,1'-螺二氢茚-7,7'-二酚(SPINOL)为骨架的手性磷酸已经被广泛应用于不对称催化领域, 在数以百计的反应中表现出了优秀的对映选择性. 然而在位阻较小且不含芳环的底物参与的不对称催化反应中, 这两类手性磷酸所表现出的对映选择性通常不理想, 主要原因在于BINOL的3,3'位取代基和SPINOL的6,6'位取代基向外侧扩展的固有特性使得催化活性位点附近的手性环境相对宽松. 为了发展适用于这类底物的手性磷酸催化剂, 设计了一种以9,9'-联-10-菲酚(BIFOL)为骨架的1,1'位具有向内侧伸展的芳基取代基的具有紧密手性环境的磷酸, 以廉价易得的间二溴苯为起始原料, 首先合成关键中间体8-溴-9-菲酚, 再通过氧化偶联合成1,1'位溴代的BIFOL, 然后利用Suzuki-Miyaura偶联反应引入芳基取代基, 最后将芳基取代的BIFOL与三氯氧磷反应的产物磷酰氯水解, 经过十二步反应合成了目标分子, 并且通过单晶X射线衍射分析确定了其结构.

关键词: 手性磷酸, 紧密手性环境, 联菲酚, 9,9'-联-10-菲酚, 8-溴-9-菲酚, 有机分子催化剂, 9,9'-联-10-菲酚(BIFOL)

Chiral phosphoric acids derived from 1,1'-binaphthyl-2,2'-diol (BINOL) and 1,1'-spirobiindane-7,7'-diol (SPINOL) have been widely applied in asymmetric catalysis and displayed excellent enantioselectivities in hundreds of reactions. However, in catalytic asymmetric reactions that involve less sterically hindered nonaromatic substrates, these Brønsted acids usually provide unsatisfactory enantioselectivities due to the relatively loose chiral environment around the catalytically active site induced by the inherent orientational property of the 3,3'-substituents which extend outwardly. In order to develop chiral phosphoric acids that are compatible with these substrates, 9,9'-biphenanthryl-10,10'-diol (BIFOL)-based confined phosphoric acid was designed by introducing two aromatic substituents which extend inwardly onto the 1,1'-positions of BIFOL. By employing cheap and commercially available m-dibromobenzene as starting material, the key intermediate 8-bromophenanthren- 9-ol which undergoes oxidative coupling to afford 1,1'-dibromo-9,9'-biphenanthryl-10,10'-diol was first synthesized. After introducing two aryl substituents through Suzuki-Miyaura coupling, the obtained aryl-substituted BIFOL was converted to the targeted molecule by reacting with phosphoryl chloride and hydrolyzing. The structure of the obtained phosphoric acid was confirmed by single crystal X-ray diffraction analysis.

Key words: chiral phosphoric acid, compact chiral environment, biphenanthrol, 9,9'-biphenanthryl-10,10'-diol, 8-bromo- phenanthren-9-ol, organocatalyst, 9,9'-biphenanthryl-10,10'-diol (BIFOL)

引用此文

岑守义, 张志鹏. 具有紧密手性环境的联菲酚骨架磷酸的合成[J]. 有机化学, 2022, 42(8): 2574-2581.

Shouyi Cen, Zhipeng Zhang. Synthesis of Biphenanthrol-Based Confined Chiral Phosphoric Acid[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2574-2581.

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

分享此文

图/表 4

图1. 以BINOL和SPINOL为骨架的手性磷酸以及一种具有紧密手性环境的联菲酚骨架手性磷酸

Figure 1. BINOL- and SPINOL-based chiral phosphoric acids and design of a confined chiral phosphoric acid based on 9,9'- biphenanthrol-10,10'-diol (BIFOL)

图式1. 联菲骨架磷酸的反合成分析

Scheme 1. Retrosynthetic analysis for a BIFOL-based confined phosphoric acid

图式2. 手性磷酸PA1的合成路线

Scheme 2. Synthetic route for chiral phosphoric acid PA1

图2. 手性磷酸PA1的晶体结构图 (热椭球是在 30%的概率水平)

Figure 2. Crystal structure of chiral phosphoric acid PA1 (thermal ellipsoids at 30% probability)

参考文献 31

[1]	(a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566. doi: 10.1002/anie.200353240 pmid: 15113196
	(b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356. pmid: 15113196
[2]	(a) Akiyama, T.; Mori, K. Chem. Rev. 2015, 115, 9277. doi: 10.1021/acs.chemrev.5b00041 pmid: 22282764
	(b) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047. doi: 10.1021/cr5001496 pmid: 22282764
	(c) Xu, B.; Zhu, S.-F.; Xie, X.-L.; Shen, J.-J.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 11483. doi: 10.1002/anie.201105485 pmid: 22282764
	(d) Sedgwick, D. M.; Grayson, M. N.; Fustero, S.; Barrio, P. Synthesis 2018, 50, 1935. doi: 10.1055/s-0036-1589532 pmid: 22282764
	(e) Cheng, J. K.; Xiang, S.-H.; Li, S.; Ye, L.; Tan, B. Chem. Rev. 2021, 121, 4805. doi: 10.1021/acs.chemrev.0c01306 pmid: 22282764
	(f) Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498. doi: 10.1039/c1cs15268h pmid: 22282764
	(g) Li, S.; Xiang, S.-H.; Tan, B. Chin. J. Chem. 2020, 38, 213. pmid: 22282764
	(h) Lin, X.; Wang, L.; Han, Z.; Chen, Z. Chin. J. Chem. 2021, 39, 802. pmid: 22282764
	(i) Zhou, X.-L.; Su, Y.-L.; Wang, P.-S.; Gong, L.-Z. Acta Chim. Sinica 2018, 76, 857. (in Chinese) pmid: 22282764
	(周霄乐, 苏永亮, 汪普生, 龚流柱, 化学学报, 2018, 76, 857.) doi: 10.6023/A18060235 pmid: 22282764
	(j) Sheng, F.-T.; Li, Z.-M.; Zhang, Y.-Z.; Sun, L.-X.; Zhang, Y.-C.; Tan, W.; Shi, F. Chin. J. Chem. 2020, 38, 583. doi: 10.1002/cjoc.202000022 pmid: 22282764
	(k) Mo, N.-F.; Yu, L.; Zhang, Y.; Yao, Y.-H.; Kou, X.; Ren, Z.-H.; Guan, Z.-H. CCS Chem. 2020, 2, 1775. pmid: 22282764
	(l) Lv, X.; Liu, S.; Zhou, S.; Dong, G.; Xing, D.; Xu, X.; Hu, W. CCS Chem. 2020, 2, 1903. pmid: 22282764
[3]	(a) Yang, L.-L.; Ouyang, J.; Zou, H.-N.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2021, 143, 6401. doi: 10.1021/jacs.1c03435
	(b) Yang, L.-L.; Evans, D.; Xu, B.; Li, W.-T.; Li, M.-L.; Zhu, S.-F.; Houk, K. N.; Zhou, Q.-L. J. Am. Chem. Soc. 2020, 142, 12394. doi: 10.1021/jacs.0c04725
	(c) Li, Y.; Zhao, Y.-T.; Zhou, T.; Chen, M.-Q.; Li, Y.-P.; Huang, M.-Y.; Xu, Z.-C.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2020, 142, 10557. doi: 10.1021/jacs.0c04532
	(d) Li, M.; Chen, M.; Xu, B.; Zhu, S.; Zhou, Q. Acta Chim. Sinica 2018, 76, 883. (in Chinese) doi: 10.6023/A18060234
	(李茂霖, 陈梦青, 徐彬, 朱守非, 周其林, 化学学报, 2018, 76, 883.) doi: 10.6023/A18060234
	(e) Ren, Y.-Y.; Zhu, S.-F.; Zhou, Q.-L. Org. Biomol. Chem. 2018, 16, 3087. doi: 10.1039/C8OB00473K
	(f) Guo, J.-X.; Zhou, T.; Xu, B.; Zhu, S.-F.; Zhou, Q.-L. Chem. Sci. 2016, 7, 1104. doi: 10.1039/C5SC03558A
	(g) Xu, B.; Li, M.-L.; Zuo, X.-D.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2015, 137, 8700. doi: 10.1021/jacs.5b05086
[4]	(a) Xia, Z.-L.; Xu-Xu, Q.-F.; Zheng, C.; You, S.-L. Chem. Soc. Rev. 2020, 49, 286. doi: 10.1039/C8CS00436F
	(b) Cai, Q.; Liu, C.; Liang, X.-W.; You, S.-L. Org. Lett. 2012, 14, 4588. doi: 10.1021/ol302043s
	(c) Zhou, Y.; Xia, Z.-L.; Gu, Q.; You, S.-L. Org. Lett. 2017, 19, 762. doi: 10.1021/acs.orglett.6b03610
	(d) Xia, Z.-L.; Zheng, C.; Wang, S.-G.; You, S.-L. Angew. Chem., Int. Ed. 2018, 57, 2653. doi: 10.1002/anie.201712435
	(e) Xia, Z.-L.; Zheng, C.; Xu, R.-Q.; You, S.-L. Nat. Commun. 2019, 10, 3150. doi: 10.1038/s41467-019-11109-9
	(f) Duan, D.; Yin, Q.; Wang, S.; Gu, Q.; You, S. Acta Chim. Sinica 2014, 72, 1001. (in Chinese) doi: 10.6023/A14060497
	(段德河, 殷勤, 王守国, 顾庆, 游书力, 化学学报, 2014, 72, 1001.) doi: 10.6023/A14060497
[5]	(a) Zhang, J.; Yu, P.; Li, S.-Y.; Sun, H.; Xiang, S.-H.; Wang, J.; Houk, K. N.; Tan, B. Science 2018, 361, 1087.
	(b) Yang, J.; Zhang, J.-W.; Bao, W.; Qiu, S.-Q.; Li, S.; Xiang, S.-H.; Song, J.; Zhang, J.; Tan, B. J. Am. Chem. Soc. 2021, 143, 12924. doi: 10.1021/jacs.1c05079
	(c) An, Q.-J.; Xia, W.; Ding, W.-Y.; Liu, H.-H.; Xiang, S.-H.; Wang, Y.-B.; Zhong, G.; Tan, B. Angew. Chem., Int. Ed. 2021, 60, 24888. doi: 10.1002/anie.202111251
	(d) Mao, J.-H.; Wang, Y.-B.; Yang, L.; Xiang, S.-H.; Wu, Q.-H.; Cui, Y.; Lu, Q.; Lv, J.; Li, S.; Tan, B. Nat. Chem. 2021, 13, 982. doi: 10.1038/s41557-021-00750-x
	(e) Zhang, L.; Shen, J.; Wu, S.; Zhong, G.; Wang, Y.-B.; Tan, B. Angew. Chem., Int. Ed. 2020, 59, 23077. doi: 10.1002/anie.202010598
	(f) Xia, W.; An, Q.-J.; Xiang, S.-H.; Li, S.; Wang, Y.-B.; Tan, B. Angew. Chem., Int. Ed. 2020, 59, 6775. doi: 10.1002/anie.202000585
	(g) Wang, Y.-B.; Yu, P.; Zhou, Z.-P.; Zhang, J.; Wang, J.; Luo, S.-H.; Gu, Q.-S.; Houk, K. N.; Tan, B. Nat. Catal. 2019, 2, 504. doi: 10.1038/s41929-019-0278-7
	(h) Da, B.-C.; Xiang, S.-H.; Li, S.; Tan, B. Chin. J. Chem. 2021, 39, 1787. doi: 10.1002/cjoc.202000751
[6]	Li, S.; Zhang, J.-W.; Li, X.-L.; Cheng, D.-J.; Tan, B. J. Am. Chem. Soc. 2016, 138, 16561. doi: 10.1021/jacs.6b11435
[7]	(a) Qian, D.; Chen, M.; Bissember, A. C.; Sun, J. Angew. Chem., Int. Ed. 2018, 57, 3763. doi: 10.1002/anie.201712395 pmid: 33382271
	(b) Sun, S.; Wang, Z.; Li, S.; Zhou, C.; Song, L.; Huang, H.; Sun, J. Org. Lett. 2021, 23, 554. doi: 10.1021/acs.orglett.0c04074 pmid: 33382271
[8]	Zhang, R.; Ge, S.; Sun, J. J. Am. Chem. Soc. 2021, 143, 12445. doi: 10.1021/jacs.1c05709
[9]	(a) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32. doi: 10.1039/C9CS00681H
	(b) Zeng, Y.; Liu, X.-D.; Guo, X.-Q.; Gu, Q.-S.; Li, Z.-L.; Chang, X.-Y.; Liu, X.-Y. Sci. China Chem. 2019, 62, 1529. doi: 10.1007/s11426-019-9528-2
	(c) Lin, J.-S.; Li, T.-T.; Lin, J.-R.; Jiao, G.-Y.; Gu, Q.-S.; Cheng, J.-T.; Guo, Y.-L.; Hong, X.; Liu, X.-Y. J. Am. Chem. Soc. 2019, 141, 1074. doi: 10.1021/jacs.8b11736
	(d) Lin, J.-S.; Wang, F.-L.; Dong, X.-Y.; He, W.-W.; Yuan, Y.; Chen, S.; Liu, X.-Y. Nat. Commun. 2017, 8, 14841. doi: 10.1038/ncomms14841
	(e) Cheng, Y.-F.; Dong, X.-Y.; Gu, Q.-S.; Yu, Z.-L.; Liu, X.-Y. Angew. Chem., Int. Ed. 2017, 56, 8883. doi: 10.1002/anie.201702925
	(f) Lin, J.-S.; Dong, X.-Y.; Li, T.-T.; Jiang, N.-C.; Tan, B.; Liu, X.-Y. J. Am. Chem. Soc. 2016, 138, 9357. doi: 10.1021/jacs.6b04077
	(g) Yu, P.; Lin, J.-S.; Li, L.; Zheng, S.-C.; Xiong, Y.-P.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2014, 53, 11890. doi: 10.1002/anie.201405401
	(h) Wang, Z.; Cheng, J.-T.; Shi, Z.; Wang, N.; Zhan, F.; Jiang, S.-P.; Lin, J.-S.; Jiang, Y.; Liu, X.-Y. ChemCatChem 2021, 13, 185. doi: 10.1002/cctc.202001398
	(i) Li, X.-F.; Lin, J.-S.; Wang, J.; Li, Z.-L.; Gu, Q.-S.; Liu, X.-Y. Acta Chim. Sinica 2018, 76, 878. (in Chinese) doi: 10.6023/A18100413
	(李雪飞, 林进顺, 王建, 李忠良, 顾强帅, 刘心元, 化学学报, 2018, 76, 878.) doi: 10.6023/A18100413
	(j) Wang, F.-L.; Dong, X.-Y.; Lin, J.-S.; Zeng, Y.; Jiao, G.-Y.; Gu, Q.-S.; Guo, X.-Q.; Ma, C.-L.; Liu, X.-Y. Chem 2017, 3, 979. doi: 10.1016/j.chempr.2017.10.008
[10]	(a) Liao, G.; Zhang, T.; Jin, L.; Wang, B.-J.; Xu, C.-K.; Lan, Y.; Zhao, Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2022, 61, e202115221.
	(b) Jin, L.; Zhang, P.; Li, Y.; Yu, X.; Shi, B.-F. J. Am. Chem. Soc. 2021, 143, 12335. doi: 10.1021/jacs.1c06236
	(c) Zhan, B.-B.; Jia, Z.-S.; Luo, J.; Jin, L.; Lin, X.-F.; Shi, B.-F. Org. Lett. 2020, 22, 9693. doi: 10.1021/acs.orglett.0c03757
	(d) Zhan, B.-B.; Wang, L.; Luo, J.; Lin, X.-F.; Shi, B.-F. Angew. Chem., Int. Ed. 2020, 59, 3568. doi: 10.1002/anie.201915674
	(e) Luo, J.; Zhang, T.; Wang, L.; Liao, G.; Yao, Q.-J.; Wu, Y.-J.; Zhan, B.-B.; Lan, Y.; Lin, X.-F.; Shi, B.-F. Angew. Chem., Int. Ed. 2019, 58, 6708. doi: 10.1002/anie.201902126
[11]	(a) Guo, Z.; Xie, J.; Hu, T.; Chen, Y.; Tao, H.; Yang, X. Chem. Commun. 2021, 57, 9394. doi: 10.1039/D1CC03117A
	(b) Tang, M.; Gu, H.; He, S.; Rajkumar, S.; Yang, X. Angew. Chem., Int. Ed. 2021, 60, 21334. doi: 10.1002/anie.202106151
	(c) Pan, Y.; Wang, D.; Chen, Y.; Zhang, D.; Liu, W.; Yang, X. ACS Catal. 2021, 11, 8443. doi: 10.1021/acscatal.1c02331
	(d) Chen, Y.; Zhu, C.; Guo, Z.; Liu, W.; Yang, X. Angew. Chem., Int. Ed. 2021, 60, 5268. doi: 10.1002/anie.202015008
	(e) Pan, Y.; Jiang, Q.; Rajkumar, S.; Zhu, C.; Xie, J.; Yu, S.; Chen, Y.; He, Y.-P.; Yang, X. Adv. Syn. Catal. 2021, 363, 200. doi: 10.1002/adsc.202001051
	(f) Liu, W.; Jiang, Q.; Yang, X. Angew. Chem., Int. Ed. 2020, 59, 23598. doi: 10.1002/anie.202009395
	(g) He, F.; Shen, G.; Yang, X. Chin. J. Chem. 2022, 40, 15. doi: 10.1002/cjoc.202100514
[12]	(a) Zhang, Y.-C.; Jiang, F.; Shi, F. Acc. Chem. Res. 2020, 53, 425. doi: 10.1021/acs.accounts.9b00549
	(b) Li, T.-Z.; Liu, S.-J.; Sun, Y.-W.; Deng, S.; Tan, W.; Jiao, Y.; Zhang, Y.-C.; Shi, F. Angew. Chem., Int. Ed. 2021, 60, 2355. doi: 10.1002/anie.202011267
	(c) Ma, C.; Jiang, F.; Sheng, F.-T.; Jiao, Y.; Mei, G.-J.; Shi, F. Angew. Chem., Int. Ed. 2019, 58, 3014. doi: 10.1002/anie.201811177
	(d) Tan, W.; Li, X.; Gong, Y.-X.; Ge, M.-D.; Shi, F. Chem. Commun. 2014, 50, 15901. doi: 10.1039/C4CC07246D
	(e) Shi, F.; Zhang, H.-H.; Sun, X.-X.; Liang, J.; Fan, T.; Tu, S.-J. Chem. Eur. J. 2015, 21, 3465. doi: 10.1002/chem.201405245
	(f) Zhao, J.-J.; Sun, S.-B.; He, S.-H.; Wu, Q.; Shi, F. Angew. Chem., Int. Ed. 2015, 54, 5460. doi: 10.1002/anie.201500215
	(g) Wang, J.-Y.; Sun, M.; Yu, X.-Y.; Zhang, Y.-C.; Tan, W.; Shi, F. Chin. J. Chem. 2021, 39, 2163. doi: 10.1002/cjoc.202100214
[13]	(a) Birman, V. B.; Rheingold, A. L.; Lam, K.-C. Tetrahedron: Asymmetry 1999, 10, 125.
	(b) Zhang, J.-H.; Liao, J.; Cui, X.; Yu, K.-B.; Zhu, J.; Deng, J.-G.; Zhu, S.-F.; Wang, L.-X.; Zhou, Q.-L.; Chung, L. W.; Ye, T. Tetrahedron: Asymmetry 2002, 13, 1363.
	(c) Brunel, J. M. Chem. Rev. 2005, 105, 857. doi: 10.1021/cr040079g
[14]	(a) Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siegel, M. G.; Hoffman, D. H.; Sogah, G. D. Y. J. Org. Chem. 1978, 43, 1930. doi: 10.1021/jo00404a019
	(b) Chen, X.-H.; Xu, X.-Y.; Liu, H.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2006, 128, 14802. doi: 10.1021/ja065267y
	(c) Furuno, H.; Kambara, T.; Tanaka, Y.; Hanamoto, T.; Kagawa, T.; Inanaga, J. Tetrahedron Lett. 2003, 44, 6129. doi: 10.1016/S0040-4039(03)01460-6
	(d) Shigeyoshi, K.; Nobuyuki, T.; Masatoshi, M.; Hiroshi, S. Bull. Chem. Soc. Jpn. 1987, 60, 2307. doi: 10.1246/bcsj.60.2307
	(e) Frankland, P. F.; Twiss, D. F. J. Chem. Soc. Trans. 1904, 85, 1666. doi: 10.1039/CT9048501666
	(f) Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Adv. Synth. Catal. 2005, 347, 1523. doi: 10.1002/adsc.200505167
[15]	(a) Desai, A. A.; Wulff, W. D. Synthesis 2010, 3670.
	(b) Bao, J.; Wulff, W. D.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3814. doi: 10.1021/ja00062a073
	(c) Bao, J.; Wulff, W. D.; Dominy, J. B.; Fumo, M. J.; Grant, E. B.; Rob, A. C.; Whitcomb, M. C.; Yeung, S. M.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 3392. doi: 10.1021/ja952018t
	(d) Hu, G.; Holmes, D.; Gendhar, B. F.; Wulff, W. D. J. Am. Chem. Soc. 2009, 131, 14355. doi: 10.1021/ja903820m
	(e) Ding, Z.; Osminski, W. E. G.; Ren, H.; Wulff, W. D. Org. Process Res. Dev. 2011, 15, 1089. doi: 10.1021/op200088b
	(f) Desai, A. A.; Huang, L.; Wulff, W. D.; Rowland, G. B.; Antilla, J. C. Synthesis 2010, 2106.
[16]	(a) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696. pmid: 19905027
	(b) Li, G.; Liang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 5830. doi: 10.1021/ja070519w pmid: 19905027
	(c) Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084. pmid: 19905027
	(d) Zheng, W.; Zhang, Z.; Kaplan, M. J.; Antilla, J. C. J. Am. Chem. Soc. 2011, 133, 3339. doi: 10.1021/ja109824x pmid: 19905027
	(e) Larson, S. E.; Li, G.; Rowland, G. B.; Junge, D.; Huang, R.; Woodcick, H. L.; Antilla, J. C. Org. Lett. 2011, 13, 2188. doi: 10.1021/ol200407r pmid: 19905027
	(f) Larson, S. E.; Baso, J. C.; Li, G.; Antilla, J. C. Org. Lett. 2009, 11, 5186. doi: 10.1021/ol902123h pmid: 19905027
[17]	(a) Lee, S.; Kim, S. Tetrahedron Lett. 2009, 50, 3345. doi: 10.1016/j.tetlet.2009.02.136
	(b) Lu, G.; Birman, V. B. Org. Lett. 2011, 13, 356. doi: 10.1021/ol102736t
	(c) Zhuang, M.; Du, H. Org. Biomol. Chem. 2013, 11, 1460. doi: 10.1039/c3ob27285k
	(d) Liao, S.; Čoric, I.; Wang, Q.; List, B. J. Am. Chem. Soc. 2012, 134, 10765. doi: 10.1021/ja3035637
	(e) Zhang, Q.-W.; Fan, C.-A.; Zhang, H.-J.; Tu, Y.-Q.; Zhao, Y.-M.; Gu, P.; Chen, Z.-M. Angew. Chem., Int. Ed. 2009, 48, 8572. doi: 10.1002/anie.200904565
	(f) Huang, D.; Wang, H.; Xue, F.; Guan, H.; Li, L.; Peng, X.; Shi, Y. Org. Lett. 2011, 13, 6350. doi: 10.1021/ol202527g
	(g) Terada, M.; Tanaka, H.; Sorimachi, K. Synlett 2008, 1661.
[18]	(a) Čorić, I.; List, B. Nature 2012, 483, 315. doi: 10.1038/nature10932
	(b) Das, S.; Liu, L.; Zheng, Y.; Alachraf, M. W.; Thiel, W.; De, C. K.; List, B. J. Am. Chem. Soc. 2016, 138, 9429. doi: 10.1021/jacs.6b06626
	(c) Liu, L.; Kaib, P. S. J.; Tap, A.; List, B. J. Am. Chem. Soc. 2016, 138, 10822. doi: 10.1021/jacs.6b07240
	(d) Schreyer, L.; Properzi, R.; List, B. Angew. Chem., Int. Ed. 2019, 58, 12761. doi: 10.1002/anie.201900932
[19]	(a) Grossmann, O.; Maji, R.; Aukland, M. H.; Lee, S.; List, B. Angew. Chem., Int. Ed. 2022, 61, doi: 10.1002/anie.202115036. doi: 10.1002/anie.202115036 pmid: 30277760
	(b) Díaz-Oviedo, C. D.; Maji, R.; List, B. J. Am. Chem. Soc. 2021, 143, 20598. doi: 10.1021/jacs.1c10245 pmid: 30277760
	(c) Das, S.; Mitschke, B.; De, C. K.; Harden, I.; Bistoni, G.; List, B. Nat. Catal. 2021, 4, 1043. doi: 10.1038/s41929-021-00714-x pmid: 30277760
	(d) Amatov, T.; Tsuji, N.; Maji, R.; Schreyer, L.; Zhou, H.; Leutzsch, M.; List, B. J. Am. Chem. Soc. 2021, 143, 14475. doi: 10.1021/jacs.1c07447 pmid: 30277760
	(e) Ghosh, S.; Das, S.; De, C. K.; Yepes, D.; Neese, F.; Bistoni, G.; Leutzsch, M.; List, B. Angew. Chem., Int. Ed. 2020, 59, 12347. doi: 10.1002/anie.202000307 pmid: 30277760
	(f) Schreyer, L.; Kaib, P. S. J.; Wakchaure, V. N.; Obradors, C.; Properzi, R.; Lee, S.; List, B. Science 2018, 362, 216. doi: 10.1126/science.aau0817 pmid: 30277760
	(g) Gatzenmeier, T.; Turberg, M.; Yepes, D.; Xie, Y.; Neese, F.; Bistoni, G.; List, B. J. Am. Chem. Soc. 2018, 140, 12671. doi: 10.1021/jacs.8b07092 pmid: 30277760
[20]	(a) Yamamoto, K.; Fukushima, H.; Nakazaki, M. J. Chem. Soc., Chem. Commun. 1984, 1490.
	(b) Yamamoto, K.; Fukushima, H.; Okamoto, Y.; Hatada, K.; Nakazaki, M. J. Chem. Soc., Chem. Commun. 1984, 1111.
[21]	(a) Takizawa, S.; Kodera, J.; Yoshida, Y.; Sako, M.; Breukers, S.; Enders, D.; Sasai, H. Tetrahedron 2014, 70, 1786. doi: 10.1016/j.tet.2014.01.017
	(b) Xie, S.; Wu, F.; Huang, W. Acta Sci. Nat. Univ. Sunyatseni 1986, 25, 18. (in Chinese)
	(谢颂凯, 吴峰, 黄文洪, 中山大学学报(自然科学版), 1986, 25, 18.)
[22]	(a) Takizawa, S.; Katayama, T.; Kameyama, C.; Onitsuka, K.; Suzuki, T.; Yanagida, T.; Kawaia, T.; Sasai, H. Chem. Commun. 2008, 1810.
	(b) Takizawa, S.; Rajesh, D.; Katayama, T.; Sasai, H. Synlett 2009, 1667.
	(c) Aydin, J.; Kumar, K. S.; Sayah, M. J.; Wallner, O. A.; Szabó, K. J. J. Org. Chem. 2007, 72, 4689. doi: 10.1021/jo070288b
[23]	Saá, J. M.; Morey, J.; Frontera, A.; Deyá, P. M. J. Am. Chem. Soc. 1995, 117, 1105. doi: 10.1021/ja00108a029
[24]	(a) Gualandi, A.; Savoini, A.; Saporetti, R.; Franchi, P.; Lucarini, M.; Cozzi, P. G. Org. Chem. Front. 2018, 5, 1573. doi: 10.1039/C8QO00061A pmid: 18454526
	(b) Norman, D. W.; Carraz, C. A.; Hyett, D. J.; Pringle, P. G.; Sweeney, J. B.; Orpen, A. G.; Phetmung, H.; Wingad, R. L. J. Am. Chem. Soc. 2008, 130, 6840. doi: 10.1021/ja800858x pmid: 18454526
	(c) Gao, H.; Zhou, Z.; Kwon, D.-H.; Coombs, J.; Jones, S.; Behnke, N. E.; Ess, D. H.; Kürti, L. Nat. Chem. 2017, 9, 681. doi: 10.1038/nchem.2672 pmid: 18454526
	(d) Furusho, Y.; Tsunoda, A.; Aida, T. J. Chem. Soc., Perkin Trans. 1 1996, 183. pmid: 18454526
[25]	Snieckus, V. Chem. Rev. 1990, 90, 879. doi: 10.1021/cr00104a001
[26]	Luliński, S.; Serwatowski, J. J. Org. Chem. 2003, 68, 5384. doi: 10.1021/jo0340511
[27]	Tashiro, M.; Nakayama, K. Org. Prep. Proced. Int. 1984, 16, 379. doi: 10.1080/00304948409457894
[28]	(a) Eaton, P. E.; Martin, R. M. J. Org. Chem. 1988, 53, 2728. doi: 10.1021/jo00247a013
	(b) Leggio, A.; Belsito, E. L.; Luca, G. D.; Gioia, M. L. D.; Leotta, V.; Romio, E.; Sicilianoa, C.; Liguori, A. RSC Adv. 2016, 6, 34468. doi: 10.1039/C5RA24527C
[29]	Jørgensen, K. B.; Rantanen, T.; Dörfler, T.; Snieckus, V. J. Org. Chem. 2015, 80, 9410. doi: 10.1021/acs.joc.5b01300 pmid: 26301487
[30]	(a) Nakajima, K.; Kojimo, M.; Fujita, J. Chem. Lett. 1986, 15, 1483. doi: 10.1246/cl.1986.1483 pmid: 11263903
	(b) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869. pmid: 11263903
[31]	Lim, J. Y. C.; Marques, I.; Félix, V.; Beer, P. D. J. Am. Chem. Soc. 2017, 139, 12228. doi: 10.1021/jacs.7b06144