Enantioselective Indium-Catalyzed Transformations

Abstract

This review updates the field of enantioselective indium-catalyzed transformations of all types since 2012. It shows that asymmetric indium catalysis, that suits the growing demand for greener processes, offers a real opportunity to replace toxic metals in the near future.

1 Introduction

2 Allylations, Propargylations, and Allenylations of Carbonyl Compounds and Derivatives

2.1 Allylations

2.2 Propargylations and Allenylations

3 Cycloadditions

3.1 Hetero-Diels–Alder Cycloadditions

3.2 1,3-Dipolar Cycloadditions

4 Miscellaneous Reactions

5 Domino and Tandem Reactions

6 Conclusion

Keywords

asymmetric indium catalysis - enantioselective reactions - metal catalysis - chirality - asymmetric catalysis

Publication History

Received: 01 December 2020

Accepted after revision: 08 January 2021

Accepted Manuscript online:
08 January 2021

Article published online:
09 February 2021

• References

• 1 Chao L.-C, Rieke RD. J. Org. Chem. 1975; 40: 2253
• 2 Araki S, Ito H, Butsugan Y. J. Org. Chem. 1988; 53: 1831
• 3 Li Y, Xu M.-H. In Indium: Properties, Technological Applications and Health Issues . Woo HG, Choi HT. Nova Science; New York: 2013: 187-217
• 4a Podlech J, Maier TC. Synthesis 2003; 633
• 4b Frost CG, Hartley JP. Mini-Rev. Org. Chem. 2004; 1: 1
• 4c Araki S, Hirashita T. In Main Group Metals in Organic Synthesis . Yamamoto H, Oshima K. Wiley-VCH; Weinheim: 2004: 323-386
• 4d Ghosh R, Maiti S. J. Mol. Catal.: A 2007; 264: 1
• 5a Cintas P. Synlett 1995; 1087
• 5b Li C.-J, Chan T.-H. Tetrahedron 1999; 55: 11149
• 5c Ranu BC. Eur. J. Org. Chem. 2000; 2347
• 5d Nair V, Ros S, Jayan CN, Pillai BS. Tetrahedron 2004; 60: 1959
• 5e Augé J, Lubin-Germain N, Uziel J. Synthesis 2007; 1739
• 6 Yang Y.-S, Wang S.-W, Long Y. Curr. Org. Chem. 2016; 20: 2865
• 7a Roy UK, Roy S. Chem. Rev. 2010; 110: 2472
• 7b Shen Z.-L, Wang S.-Y, Chok Y.-K, Xu Y.-H, Loh T.-P. Chem. Rev. 2013; 113: 271
• 8a Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207
• 8b Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
• 8c Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2013; 113: 5595
• 8d Lumbroso A, Cooke ML, Breit B. Angew. Chem. Int. Ed. 2013; 52: 1890
• 8e Huo H, Duvall JR, Huang M.-Y, Hong R. Org. Chem. Front. 2014; 1: 303
• 9 Kargbo R, Cook GR. Curr. Org. Chem. 2007; 11: 1287
• 10 Loh T.-P, Zhou J.-R, Li X.-R. Tetrahedron Lett. 1999; 40: 9333
• 11 Cook GR, Kargbo R, Maity B. Org. Lett. 2005; 7: 2767
• 12a Murata Y, Takahashi M, Yagishita F, Sakamoto M, Sengoku T, Yoda H. Org. Lett. 2013; 15: 6182
• 12b Takahashi M, Murata Y, Yagishita F, Sakamoto F, Sengoku T, Yoda H. Chem. Eur. J. 2014; 20: 11091
• 13 Kitson RA, Millemaggi A, Taylor RJ. K. Angew. Chem. Int. Ed. 2009; 48: 9426
• 14 Takahashi M, Murata Y, Ishida M, Yagishita F, Sakamoto M, Sengokua T, Yoda H. Org. Biomol. Chem. 2014; 12: 7686
• 15 Nakamura S, Hara Y, Furukawa T, Hirashita T. RSC Adv. 2017; 7: 15582
• 16a Chakrabarti A, Konishi H, Yamaguchi M, Schneider U, Kobayashi S. Angew. Chem. Int. Ed. 2010; 49: 1838
• 16b Huang Y.-Y, Chakrabarti A, Morita N, Schneider U, Kobayashi S. Angew. Chem. Int. Ed. 2011; 50: 11121
• 17 Schneider U, Kobayashi S. Acc. Chem. Res. 2012; 45: 1331
• 18 Chen T, Cai C. Org. Biomol. Chem. 2016; 14: 5019
• 19 Kumar D, Vemula SR, Balasubramanian N, Cook GR. Acc. Chem. Res. 2016; 49: 2169
• 20 Sengoku T, Kokubo K, Sakamoto M, Takahashi M, Yoda H. Org. Biomol. Chem. 2017; 15: 320
• 21 Loh T.-P, Lin M.-J, Tan K.-L. Tetrahedron Lett. 2003; 44: 507
• 22 Haddad TD, Hirayama LC, Buckley JJ, Singaram B. J. Org. Chem. 2012; 77: 889
• 23 Sengoku T, Ikeda I, Ai K, Takahashi M, Yoda H. Org. Biomol. Chem. 2019; 17: 2614
• 24 Ali T, Chauhan KK, Frost CG. Tetrahedron Lett. 1999; 40: 5621
• 25 Lv J, Zhang L, Hu S, Cheng J.-P, Luo S. Chem. Eur. J. 2012; 18: 799
• 26 Zhao B, Loh T.-P. Org. Lett. 2013; 15: 2914
• 27 Heravi MM, Ahmadi T, Ghavidel M, Heidari B, Hamidi H. RSC Adv. 2015; 5: 101999
• 28 Wang L, Lv J, Zhang L, Luo S. Angew. Chem. Int. Ed. 2017; 56: 10867
• 29 Li S, Lv J, Luo S. Org. Chem. Front. 2018; 5: 1787
• 30a Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
• 30b Pellissier H. Tetrahedron 2007; 63: 3235
• 30c Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887
• 30d Kissane M, Maguire AR. Chem. Soc. Rev. 2010; 39: 845
• 30e Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
• 30f Singh MS, Chowdhury S, Koley S. Tetrahedron 2016; 72: 1603
• 30g Klier L, Tur F, Poulsen PH, Jørgensen KA. Chem. Soc. Rev. 2017; 46: 1080
• 31 Zhang M, Kumagai N, Shibasaki M. Chem. Eur. J. 2017; 23: 12450
• 32 Clarke ML, France MB. Tetrahedron 2008; 64: 9003
• 33 Zhang X, Wang M, Ding R, Xu Y.-H, Loh T.-P. Org. Lett. 2015; 17: 2736
• 34 Gao B, Xie M, Sun A, Hu X, Ding X, Liu X, Lin L, Feng X. Adv. Synth. Catal. 2012; 354: 1509
• 35 Capdevila MG, Emer E, Benfatti F, Gualandi A, Wilson CM, Cozzi PG. Asian J. Org. Chem. 2012; 1: 38
• 36 Gualandi A, Mengozzi L, Wilson CM, Cozzi PG. Synthesis 2014; 46: 1321
• 37 Volla CM. R, Fava E, Atodiresei I, Rueping M. Chem. Commun. 2015; 51: 15788
• 38 Praveen C, Montaignac B, Vitale MR, Ratovelomanana-Vidal V, Michelet V. ChemCatChem 2013; 5: 2395
• 39 Casiraghi G, Battistini L, Curti C, Rassu G, Zanardi F. Chem. Rev. 2011; 111: 3076
• 40 Fu K, Zheng J, Lin L, Liu X, Feng X. Chem. Commun. 2015; 51: 3106
• 41 Rout S, Das A, Singh VK. J. Org. Chem. 2018; 83: 5058
• 42a Ho T.-L. Tandem Organic Reactions 1992
• 42b Bunce RA. Tetrahedron 1995; 51: 13103
• 42c Padwa A, Weingarten MD. Chem. Rev. 1996; 96: 223
• 42d Denmark SE, Thorarensen A. Chem. Rev. 1996; 96: 137
• 42e Hulme C, Gore V. Curr. Med. Chem. 2003; 10: 51
• 42f Tietze LF, Rackelmann N. Pure Appl. Chem. 2004; 76: 1967
• 42g Fogg DE, dos Santos EN. Coord. Chem. Rev. 2004; 248: 2365
• 42h Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
• 42i Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
• 42j Chapman CJ, Frost CG. Synthesis 2007; 1
• 42k Padwa A, Bur SK. Tetrahedron 2007; 63: 5341
• 42l D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
• 42m Alba A.-N, Companyo X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
• 42n Themed collection on Rapid Complexity Generation in Natural Product Total Synthesis: Davies HM. L, Sorensen EJ. Eds. Chem. Soc. Rev. 2009; 38: 2981-3272
• 42o Nicolaou KC, Chen JS. Chem. Soc. Rev. 2009; 38: 2993
• 42p Ruiz M, Lopez-Alvarado P, Giorgi G, Menéndez JC. Chem. Soc. Rev. 2011; 40: 3445
• 42q De Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
• 42r Ardkhean R, Caputo DF. J, Morrow SM, Shi H, Xiong Y, Anderson EA. Chem. Soc. Rev. 2016; 45: 1557
• 42s Hayashi Y. Chem. Sci. 2016; 7: 866
• 43a Posner GH. Chem. Rev. 1986; 86: 831
• 43b Tietze LF, Beifuss U. Angew. Chem., Int. Ed. Engl. 1993; 32: 131
• 43c Tietze LF. Chem. Rev. 1996; 96: 115
• 43d Parsons PJ, Penkett CS, Shell AJ. Chem. Rev. 1996; 96: 195
• 43e Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
• 43f Ramon DJ, Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
• 43g Multicomponent Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
• 43h Tietze LF, Brasche G, Gericke K. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
• 43i Pellissier H. Tetrahedron 2006; 62: 2143
• 43j Pellissier H. Tetrahedron 2006; 62: 1619
• 43k Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
• 43l Guillena G, Ramon DJ, Yus M. Tetrahedron: Asymmetry 2007; 18: 693
• 43m Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
• 43n Synthesis of Heterocycles via Multicomponent Reactions I. In Topics in Heterocyclic Chemistry, Vol. 23. Orru RV. A, Ruijter E. Springer; Berlin: 2010
• 43o Synthesis of Heterocycles via Multicomponent Reactions II. In Topics in Heterocyclic Chemistry, Vol. 25. Orru RV. A, Ruijter E. Springer; Berlin: 2010
• 43p Pellissier H. Adv. Synth. Catal. 2012; 354: 237
• 43q Clavier H, Pellissier H. Adv. Synth. Catal. 2012; 354: 3347
• 43r Pellissier H. Chem. Rev. 2013; 113: 442
• 43s Pellissier H. Asymmetric Domino Reactions . RSC; Cambridge: 2013
• 43t Domino Reactions: Concepts for Efficient Organic Synthesis. Tietze LF. Wiley-VCH; Weinheim: 2014
• 43u Multicomponent Reactions in Organic Synthesis . Zhu J, Wang Q, Wang M. Wiley-VCH; Weinheim: 2014
• 43v Multicomponent Reactions: Concepts and Applications for Design and Synthesis. Herrera RP, Marqués-López E. Wiley; Hoboken: 2015
• 43w Snyder SA. Science of Synthesis: Applications of Domino Transformations in Organic Synthesis. Georg Thieme Verlag; Stuttgart: 2016
• 43x Pellissier H. Adv. Synth. Catal. 2016; 358: 2194
• 43y Pellissier H. Adv. Synth. Catal. 2019; 361: 1733
• 44 Trost BM, Breder A, Kai B. Org. Lett. 2012; 14: 1708
• 45 Liu Q.-J, Yan WG, Wang L, Zhang XP, Tang Y. Org. Lett. 2015; 17: 4014
• 46 Zhong X, Lv J, Luo S. Org. Lett. 2017; 19: 3331
• 47 Vilums M, Heuberger J, Heitman LH, Ijzerman AP. Med. Res. Rev. 2015; 35: 1097
• 48 Phillips AR, Blümel M, Dochain S, Hack D, Enders D. Synthesis 2017; 49: 1538
• 49 Chen Y, Dong S, Xu X, Liu X, Feng X. Angew. Chem. Int. Ed. 2018; 57: 16554