Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling

doi:10.6023/cjoc202207002

Abstract

Chiral alcohol and amine are ubiquitous in natural products and pharmaceutically relevant molecules. Thus, developing the asymmetric synthesis of these molecules is of great importance. Compared with traditional methods, transition-metal-catalyzed asymmetric dehydrogenative coupling of alcohol and amine to advanced chiral alcohol and amine has been widely studied due to its excellent step-, atom- and redox-economy. This method allows for the one-step synthesis of structurally diverse chiral alcohol and chiral amine compounds from simple starting materials. Various types of asymmetric dehydrogenative coupling upgrading reactions involving alcohols and amines according to the types of coupling reagents are summarized and the outlook on the development of the field is provided.

Key words: chiral alcohol, chiral amine, asymmetric metal catalysis, hydrogen transfer, dehydrogenative coupling, carbon- carbon bond-forming reaction

Cite this article

Binyang Jiang, Shi-Liang Shi. Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3263-3279.

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Fig. & Tab. 21

Figure 1. Drugs and natural products containing chiral alcohol or amine

Scheme 1. Several methods for synthesizing chiral alcohol and amine

Scheme 2. Iridium-catalyzed asymmetric dehydrogenative coupling of allylic acetate and benzylic alcohol

Scheme 3. Iridium-catalyzed asymmetric dehydrogenative coupling of α-methyl allylic acetate and primary alcohol

Scheme 4. Iridium-catalyzed asymmetric dehydrogenative coupling of epoxide and primary alcohol

Scheme 5. Propargyl electrophile involved asymmetric dehydrogenative coupling with primary alcohol1

Scheme 6. Ruthenium-catalyzed asymmetric dehydrogenative coupling of internal alkyne and primary alcohol

Scheme 7. Catalytic cycle of ruthenium-catalyzed asymmetric dehydrogenative coupling of internal alkyne and primary alcohol

Scheme 8. Nickel-catalyzed asymmetric dehydrogenative coupling of alkyne and alcohol

Scheme 9. Ruthenium-catalyzed asymmetric dehydrogenative coupling of 2-silyl-butadiene and primary alcohol

Scheme 10. Ruthenium-catalyzed asymmetric dehydrogenative coupling of butadiene and primary alcohol

Scheme 11. Asymmetric dehydrogenative coupling of primary alcohol and various functionalized allene

Scheme 12. Asymmetric dehydrogenative coupling of primary alcohol and enyne

Scheme 13. Asymmetric dehydrogenative coupling of allylic alcohol and aryl boronic acid

Scheme 14. Nickel-catalyzed asymmetric dehydrogenative coupling of secondary alcohol and aryl boronic ester

Scheme 15. Iridium-catalyzed asymmetric dehydrogenative coupling of primary alcohol and cyclopropane

Scheme 16. Ruthenium-catalyzed asymmetric dehydrogenative coupling of benzocyclobutenone and ketol

Scheme 17. Ruthenium-catalyzed asymmetric Guerbet reaction

Scheme 18. Tantalum-catalyzed asymmetric dehydrogenative coupling of tetrahydroquinoline and norbornene

Scheme 19. Nickel-catalyzed asymmetric dehydrogenative coupling of amine and internal alkyne

Scheme 20. Nickel-catalyzed asymmetric dehydrogenative coupling of amine and styrene

References 62

[1]	(a) Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012. doi: 10.1002/anie.201006128
	(b) Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471.
[2]	(a) Fleury-Brégeot, N.; de la Fuente, V.; Castillón, S.; Claver, C. ChemCatChem 2010, 2, 1346. doi: 10.1002/cctc.201000078
	(b) Cabré, A.; Verdaguer, X.; Riera, A. Chem. Rev. 2022, 122, 269. doi: 10.1021/acs.chemrev.1c00496
	(c) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
	(d) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300. doi: 10.1021/ar700134q
	(e) Malacea, R.; Poli, R.; Manoury, E. Coord. Chem. Rev. 2010, 254, 729. doi: 10.1016/j.ccr.2009.09.033
[3]	(a) Liu, Y.-L.; Lin, X.-T. Adv. Synth. Catal. 2019, 361, 876. doi: 10.1002/adsc.201801023 pmid: 21405021
	(b) Bartlett, S. L.; Johnson, J. S. Acc. Chem. Res. 2017, 50, 2284. doi: 10.1021/acs.accounts.7b00263 pmid: 21405021
	(c) Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853. doi: 10.1021/cr078340r pmid: 21405021
	(d) Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873. doi: 10.1039/b617746h pmid: 21405021
	(e) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626. doi: 10.1021/cr100204f pmid: 21405021
[4]	(a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. doi: 10.1021/cr900202j pmid: 17576475
	(b) Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2011, 40, 1937. doi: 10.1039/c0cs00063a pmid: 17576475
	(c) Cai, Y.; Li, F.; Li, Y.-Q.; Zhang, W.-B.; Liu, F.; Shi, S.-L. Tetrahedron Lett. 2018, 59, 1073. pmid: 17576475
	(d) Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069. pmid: 17576475
	(e) Guillena, G.; Ramón D. J. Hydrogen Transfer Reactions, Springer, Switzerland, 2016. pmid: 17576475
	(f) Kim, S. W.; Zhang, W.; Krische, M. J. Acc. Chem. Res. 2017, 50, 2371. doi: 10.1021/acs.accounts.7b00308 pmid: 17576475
	(g) Santana, C. G.; Krische, M. J. ACS Catal. 2021, 11, 5572. doi: 10.1021/acscatal.1c01109 pmid: 17576475
[5]	Nakai, K.; Yoshida, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2014, 136, 7797. doi: 10.1021/ja500666h
[6]	(a) Hassan, A.; Montgomery, T. P.; Krische, M. J. Chem. Commun. 2012, 48, 4692. doi: 10.1039/c2cc31743e pmid: 34478276
	(b) Tsutsumi, R.; Hong, S.; Krische, M. J. Chem.-Eur. J. 2015, 21, 12903. doi: 10.1002/chem.201502499 pmid: 34478276
	(c) Isbrandt, E. S.; Nasim, A.; Zhao, K.; Newman, S. G. J. Am. Chem. Soc. 2021, 143, 14646. doi: 10.1021/jacs.1c05661 pmid: 34478276
[7]	(a) Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134. pmid: 20613891
	(b) Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 47, 5220. doi: 10.1002/anie.200801359 pmid: 20613891
	(c) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120. doi: 10.1021/ja805356j pmid: 20613891
	(d) Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024. doi: 10.1016/j.tet.2009.03.068 pmid: 20613891
[8]	Maekawa, T.; Sekizawa, H.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 7022. doi: 10.1002/anie.201102092
[9]	(a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. pmid: 12914480
	(b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem., Int. Ed. 2003, 42, 4732. doi: 10.1002/anie.200301632 pmid: 12914480
[10]	(a) Kimura, M.; Shimizu, M.; Shibata, K.; Tazoe, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2003, 42, 3392. doi: 10.1002/anie.200351182
	(b) Zanoni, G.; Gladiali, S.; Marchetti, A.; Piccinini, P.; Tredici, I.; Vidari, G. Angew. Chem., Int. Ed. 2004, 43, 846. doi: 10.1002/anie.200352743
[11]	Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340. doi: 10.1021/ja802001b pmid: 18444616
[12]	Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. doi: 10.1002/anie.200460214
[13]	Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891. doi: 10.1021/ja805722e pmid: 18841896
[14]	(a) Hassan, A.; Townsend, I. A.; Krische, M. J. Chem. Commun. 2011, 47, 10028. doi: 10.1039/c1cc14392a
	(b) Luo, G.; Xiang, M.; Krische, M. J. Org. Lett. 2019, 21, 2493. doi: 10.1021/acs.orglett.9b00508
[15]	(a) Montgomery, T. P.; Hassan, A.; Park, B. Y.; Krische, M. J. J. Am. Chem. Soc. 2012, 134, 11100. doi: 10.1021/ja303839h pmid: 22734694
	(b) Xiang, M.; Luo, G.; Wang, Y.; Krische, M. J. Chem. Commun. 2019, 55, 981. doi: 10.1039/C8CC09706B pmid: 22734694
	(c) Hassan, A.; Zbieg, J. R.; Krische, M. J. Angew. Chem., Int. Ed. 2011, 50, 3493. doi: 10.1002/anie.201100646 pmid: 22734694
[16]	Cabrera, J. M.; Krische, M. J. Angew. Chem., Int. Ed. 2019, 58, 10718. doi: 10.1002/anie.201906259
[17]	Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514. doi: 10.1021/ja808857w pmid: 19191498
[18]	Gao, X.; Zhang, Y. J.; Krische, M. J. Angew. Chem., Int. Ed. 2011, 50, 4173. doi: 10.1002/anie.201008296
[19]	Han, S. B.; Gao, X.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 9153. doi: 10.1021/ja103299f
[20]	Zhang, Y. J.; Yang, J. H.; Kim, S. H.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 4562. doi: 10.1021/ja100949e pmid: 20225853
[21]	Feng, J.; Garza, V. J.; Krische, M. J. J. Am. Chem. Soc. 2014, 136, 8911. doi: 10.1021/ja504625m
[22]	Guo, Y.-A.; Lee, W.; Krische, M. J. Chem.-Eur. J. 2017, 23, 2557. doi: 10.1002/chem.201606046
[23]	Feng, J.; Noack, F.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 12364. doi: 10.1021/jacs.6b08902
[24]	Wang, G.; Franke, J.; Ngo, C. Q.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 7915. doi: 10.1021/jacs.5b04404
[25]	Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2017, 60, 1638. doi: 10.1021/acs.jmedchem.6b01367
[26]	Woo, S. K.; Geary, L. M.; Krische, M. J. Angew. Chem., Int. Ed. 2012, 51, 7830. doi: 10.1002/anie.201203334
[27]	Liang, T.; Woo, S. K.; Krische, M. J. Angew. Chem., Int. Ed. 2016, 55, 9207. doi: 10.1002/anie.201603575
[28]	Liang, T.; Nguyen, K. D.; Zhang, W.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 3161. doi: 10.1021/jacs.5b00747 pmid: 25734220
[29]	Gellrich, U.; Meißner, A.; Steffani, A.; Kä hny, M.; Drexler, H.-J.;
[30]	Heller, D.; Plattner, D. A.; Breit, B. J. Am. Chem. Soc. 2014, 136, 1097. doi: 10.1021/ja411204d
[31]	Park, B. Y.; Nguyen, K. D.; Chaulagain, M. R.; Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2014, 136, 11902. doi: 10.1021/ja505962w
[32]	Xiang, M.; Ghosh, A.; Krische, M. J. J. Am. Chem. Soc. 2021, 143, 2838. doi: 10.1021/jacs.0c12242 pmid: 33555867
[33]	Ortiz, E.; Chang, Y.-H.; Shezaf, J. Z.; Shen, W.; Krische, M. J. J. Am. Chem. Soc. 2022, 144, 8861. doi: 10.1021/jacs.2c03614
[34]	Liang, T.; Zhang, W.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 16024. doi: 10.1021/jacs.5b12131 pmid: 26671223
[35]	Cai, Y.; Zhang, J.-W.; Li, F.; Liu, J.-M.; Shi, S.-L. ACS Catal. 2019, 9, 1. doi: 10.1021/acscatal.8b04198
[36]	Ho, C.-Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782. doi: 10.1002/anie.200603907
[37]	Zbieg, J. R.; Moran, J.; Krische, M. J. J. Am. Chem. Soc. 2011, 133, 10582. doi: 10.1021/ja2046028
[38]	Zbieg, J. R.; Yamaguchi, E.; McInturff, E. L.; Krische, M. J. Science 2012, 336, 324. doi: 10.1126/science.1219274
[39]	McInturff, E. L.; Yamaguchi, E.; Krische, M. J. J. Am. Chem. Soc. 2012, 134, 20628. doi: 10.1021/ja311208a pmid: 23234459
[40]	Han, S. B.; Kim, I. S.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 6916. doi: 10.1021/ja902437k
[41]	Spielmann, K.; Xiang, M.; Schwartz, L. A.; Krische, M. J. J. Am. Chem. Soc. 2019, 141, 14136. doi: 10.1021/jacs.9b08715 pmid: 31465211
[42]	Xiang, M.; Pfaffinger, D. E.; Ortiz, E.; Brito, G. A.; Krische, M. J. J. Am. Chem. Soc. 2021, 143, 8849. doi: 10.1021/jacs.1c03480 pmid: 34060818
[43]	Geary, L. M.; Woo, S. K.; Leung, J. C.; Krische, M. J. Angew. Chem., Int. Ed. 2012, 51, 2972. doi: 10.1002/anie.201200239
[44]	Nguyen, K. D.; Herkommer, D.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 5238. doi: 10.1021/jacs.6b02279 pmid: 27079149
[45]	(a) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. doi: 10.1002/anie.201101379
	(b) Fyfe, J. W. B.; Watson, A. J. B. Chem 2017, 3, 31. doi: 10.1016/j.chempr.2017.05.008
[46]	(a) Duan, H.-F.; Xie, J.-H.; Shi, W.-J.; Zhang, Q.; Zhou, Q.-L. Org. Lett. 2006, 1479.
	(b) Tomita, D.; Kanai, M.; Shibasaki, M. Chem.-Asian. J. 2006, 1, 161. doi: 10.1002/asia.200600068
	(c) Duan, H.-F.; Xie, J.-H.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2008, 47, 4351. doi: 10.1002/anie.200800423
	(d) Li, R.; Luo, K.; Hu, Y.; Tang, W. Adv. Synth. Catal. 2013, 355, 1297. doi: 10.1002/adsc.201201125
	(e) Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353. doi: 10.1002/anie.200600392
[47]	Casnati, A.; Lichosyt, D.; Lainer, B.; Veth, L.; Dydio, P. Org. Lett. 2021, 23, 3502. doi: 10.1021/acs.orglett.1c00939
[48]	Cai, Y.; Shi, S.-L. J. Am. Chem. Soc. 2021, 143, 11963. doi: 10.1021/jacs.1c06614
[49]	(a) Cai, Y.; Ruan, L.-X.; Rahman, A.; Shi, S.-L. Angew. Chem., Int. Ed. 2021, 60, 5262. doi: 10.1002/anie.202015021
	(b) Cai, Y.; Yang, X.-T.; Zhang, S.-Q.; Li, F.; Li, Y.-Q.; Ruan, L.-X.; Hong, X.; Shi, S.-L. Angew. Chem., Int. Ed. 2018, 57, 1376. doi: 10.1002/anie.201711229
	(c) Zhang, W.-B.; Yang, X.-T.; Ma, J.-B.; Su, Z.-M.; Shi, S.-L. J. Am. Chem. Soc. 2019, 141, 5628. doi: 10.1021/jacs.9b00931
	(d) Cai, Y.; Ye, X.; Liu, S.; Shi, S.-L. Angew. Chem., Int. Ed. 2019, 58, 13433. doi: 10.1002/anie.201907387
	(e) Shen, D.; Zhang, W.-B.; Li, Z.; Shi, S.-L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 112.
	(f) Li, Y.-Q.; Li, F.; Shi, S.-L. Chin. J. Chem. 2020, 38, 1035. doi: 10.1002/cjoc.202000019
	(g) Wang, Z.-C.; Gao, J.; Cai, Y.; Ye, X.; Shi, S.-L. CCS Chem. 2022, 4, 1169. doi: 10.31635/ccschem.021.202101001
	(h) Ma, J.-B.; Zhao, X.; Zhang, D.; Shi, S.-L. J. Am. Chem. Soc. 2022, 144, 13643. doi: 10.1021/jacs.2c04043
[50]	Moran, J.; Smith, A. G.; Carris, R. M.; Johnson, J. S.; Krische, M. J. J. Am. Chem. Soc. 2011, 133, 18618. doi: 10.1021/ja2090993
[51]	Ambler, B. R.; Turnbull, B. W. H.; Suravarapu, S. R.; Uteuliyev, M. M.; Huynh, N. O.; Krische, M. J. J. Am. Chem. Soc. 2018, 140, 9091. doi: 10.1021/jacs.8b05724 pmid: 29992811
[52]	Bender, M.; Turnbull, B. W. H.; Ambler, B. R.; Krische, M. J. Science 2017, 357, 779. doi: 10.1126/science.aao0453
[53]	Wang, K.; Zhang, L.; Tang, W.; Sun, H.; Xue, D.; Lei, M.; Xiao, J.; Wang, C. Angew. Chem., Int. Ed. 2020, 59, 11408. doi: 10.1002/anie.202003104
[54]	Ng, T. W.; Liao, G.; Lau, K. K.; Pan, H.-J.; Zhao, Y. Angew. Chem., Int. Ed. 2020, 59, 11384. doi: 10.1002/anie.202004758
[55]	(a) Xu, R.; Wang, K.; Liu, H.; Tang, W.; Sun, H.; Xue, D.; Xiao, J.; Wang, C. Angew. Chem., Int. Ed. 2020, 59, 21959. doi: 10.1002/anie.202009754
	(b) Zhang, X.; Ma, W.; Zhang, J.; Tang, W.; Xue, D.; Xiao, J.; Sun, H.; Wang, C. Angew. Chem., Int. Ed. 2022, 61, e202203244.
	(c) Li, F.; Long, L.; He, Y.-M.; Li, Z.; Chen, H.; Fan, Q. H. Angew. Chem., Int. Ed. 2022, 61, e202202972.
[56]	Pan, S.; Endo, K.; Shibata, T. Org. Lett. 2011, 13, 4692. doi: 10.1021/ol201907w
[57]	Jain, P.; Verma, P.; Xia, G.; Yu, J.-Q. Nat. Chem. 2017, 9, 140. doi: 10.1038/nchem.2619
[58]	Bergonzini, G.; Schindler, C. S.; Wallentin, C.-J.; Jacobsen, E. N.; Stephenson, C. R. J. Chem. Sci. 2014, 5, 112. doi: 10.1039/C3SC52265B
[59]	(a) Herzon, S. B.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 6690. pmid: 33249842
	(b) Kubiak, R.; Prochnow, I.; Doye, S. Angew. Chem., Int. Ed. 2009, 48, 1153. doi: 10.1002/anie.200805169 pmid: 33249842
	(c) Reznichenko, A. L.; Hultzsch, K. C. J. Am. Chem. Soc. 2012, 134, 3300. doi: 10.1021/ja211945m pmid: 33249842
	(d) Koperniku, A.; Foth, P. J.; Sammis, G. M.; Schafer, L. L. J. Am. Chem. Soc. 2019, 141, 18944. doi: 10.1021/jacs.9b10465 pmid: 33249842
	(e) Bahena, E. N.; Griffin, S. E.; Schafer, L. L. J. Am. Chem. Soc. 2020, 142, 20566. doi: 10.1021/jacs.0c10405 pmid: 33249842
	(f) Yao, W.-W.; Li, R.; Chen, H.; Chen, M.-K.; Luan, Y.-X.; Wang, Y.; Yu, Z.-X.; Ye, M. Nat. Commun. 2021, 12, 3800. doi: 10.1038/s41467-021-24032-9 pmid: 33249842
[60]	Eisenberger, P.; Ayinla, R. O.; Lauzon, J. M. P.; Schafer, L. L. Angew. Chem., Int. Ed. 2009, 48, 8361. doi: 10.1002/anie.200903656
[61]	Li, Y.; Liu, Y.-C.; Shi, H. J. Am. Chem. Soc. 2021, 143, 4154. doi: 10.1021/jacs.1c00622
[62]	Yan, X.-B.; Li, Y.; Wu, W.-Q.; Xu, L.; Li, K.; Liu, Y.-C.; Shi, H. Nat. Commun. 2021, 12, 5881. doi: 10.1038/s41467-021-26194-y

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