Synthesis of Biphenanthrol-Based Confined Chiral Phosphoric Acid

doi:10.6023/cjoc202203019

Abstract

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)

Cite this article

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

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

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)

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

Scheme 2. Synthetic route for chiral phosphoric acid PA1

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

References 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

具有紧密手性环境的联菲酚骨架磷酸的合成