• This record comes from PubMed

Enantioselective Synthesis of Spiro Heterocyclic Compounds Using a Combination of Organocatalysis and Transition-Metal Catalysis

. 2023 Jul ; 23 (7) : e202200284. [epub] 20230126

Status PubMed-not-MEDLINE Language English Country United States Media print-electronic

Document type Journal Article, Review

Grant support
22-11234S Czech Science Foundation
UNCE/SCI/014. Charles University Research Centre

Over the last ten years, the combination of organocatalysis with transition metal (TM) catalysis has become one of the most important toolboxes used for synthesizing optically pure compounds containing chiral quaternary centers, including spiro heterocyclic molecules. The dominant method in the enantioselective synthesis of spiro heterocyclic compounds based on synergistic catalysis includes chiral aminocatalysis and NHC catalysis, as already established covalent organocatalytic strategies. Another area of organocatalysis widely combined with TM catalysis producing enantiomerically enriched spiro heterocyclic compounds is non-covalent catalysis, dominated by chiral phosphoric acids, thiourea, and squaramide derivatives. This review article aims to summarize enantioselective methods used for constructing spirocyclic heterocycles based on a combination of organocatalysis and transition metal catalysis.

See more in PubMed

T. T. Talele, J. Med. Chem. 2020, 63, 13291-13315.

E. Chupakhin, O. Babich, A. Prosekov, L. Asyakina, M. Krasavin, Molecules 2019, 24, 4165.

Y. Zheng, C. M. Tice, S. B. Singh, Bioorg. Med. Chem. Lett. 2014, 24, 3673-3682.

K. B. and A. M. S. S. Mohammed Benabdallah, O. Talhi, F. Nouali, N. Choukchou-Braham, Advances in Spirocyclic Hybrids: Chemistry and Medicinal Actions, Bentham Science Publisher, 2018.

K. Hiesinger, D. Dar'in, E. Proschak, M. Krasavin, J. Med. Chem. 2021, 64, 150-183.

L. F. Tietze, Chem. Rev. 1996, 96, 115-136.

R. A. Batey, J. Am. Chem. Soc. 2007, 129, 7476.

Y. Liu, Y. Wang, X. Wu, Y. R. Chi, Chem. Rec. 2022, e202200219.

F. Tanaka, Chem. Rec. 2022, e202200207.

O. García Mancheño, M. Waser, Eur. J. Org. Chem. 2022, e202200950.

B. Han, X.-H. He, Y.-Q. Liu, G. He, C. Peng, J.-L. Li, Chem. Soc. Rev. 2021, 50, 1522-1586.

M. H. Aukland, B. List, Pure Appl. Chem. 2021, 93, 1371-1381;

E. Juaristi, Tetrahedron 2021, 88, 132143.

S.-H. Xiang, B. Tan, Nat. Commun. 2020, 11, 3786.

M. P. van der Helm, B. Klemm, R. Eelkema, Nat. Chem. Rev. 2019, 3, 491-508.

A. Vega-Peñaloza, S. Paria, M. Bonchio, L. Dell'Amico, X. Companyó, ACS Catal. 2019, 9, 6058-6072.

M. Urban, J. Veselý, Enantioselective Synthesis of Spiro Heterocycles. In: Spiro Compounds: Synthesis and Applications, R. Rios (ed.), Wiley, VCH, 2022, pp. 205-282.

J.-L. Zhang, R. Ma, H.-H. Zhao, P.-F. Xu, Chem. Commun. 2022, 58, 3493-3496.

Z.-H. You, Y.-H. Chen, Y. Tang, Y.-K. Liu, Org. Lett. 2018, 20, 6682-6686.

X.-P. Chen, J.-X. Liu, H.-Y. Li, Y.-C. Xiao, F.-E. Chen, Adv. Synth. Catal. 2022, 364, 2067-2071.

B. Formánek, J. Tauchman, I. Císařová, J. Veselý, J. Org. Chem. 2020, 85, 8510-8521.

Y. Zhang, C. Wang, W. Huang, P. Haruehanroengra, C. Peng, J. Sheng, B. Han, G. He, Org. Chem. Front. 2018, 5, 2229-2233.

Y. You, W.-Y. Lu, Z.-H. Wang, Y.-Z. Chen, X.-Y. Xu, X.-M. Zhang, W.-C. Yuan, Org. Lett. 2018, 20, 4453-4457.

G.-J. Mei, F. Shi, Chem. Commun. 2018, 54, 6607-6621.

C. Cassani, X. Tian, E. C. Escudero-Adán, P. Melchiorre, Chem. Commun. 2011, 47, 233-235.

R. Westphal, E. Venturini Filho, F. Medici, M. Benaglia, S. J. Greco, Synthesis (Stuttg). 2022, 54, 2927-2975.

P.-Y. Géant, M. Urban, M. Remeš, I. Císařová, J. Veselý, Eur. J. Org. Chem. 2013, 2013, 7979-7988.

L. Li, S. Wang, P. Luo, R. Wang, Z. Wang, X. Li, Y. Deng, F. Peng, Z. Shao, Nat. Commun. 2021, 12, 5667.

P. V. Saranya, M. Neetha, T. Aneeja, G. Anilkumar, RSC Adv. 2021, 11, 7146-7179.

A. K. Franz, N. V. Hanhan, N. R. Ball-Jones, ACS Catal. 2013, 3, 540-553.

L.-Z. Gong, Enamine-Metal Combined Catalysis. In: Asymmetric Organo-Metal Catalysis: Concepts, Principles, and Applications, L.-Z. Gong (ed.), Wiley, VCH, 2022, pp. 39-74.

L.-Z. Gong, Iminium and Metal Combined Catalysis. In: Asymmetric Organo-Metal Catalysis: Concepts, Principles, and Applications, L.-Z. Gong (ed.), Wiley, VCH, 2022, pp. 75-89.

D. Castelvecchi, E. Stoye, Nature 2021, 598, 247-248.

T. Ooi, C. Crudden, ACS Catal. 2021, 11, 15234.

I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed. 2006, 45, 1952-1956;

Angew. Chem. 2006, 118, 1986-1990.

S. Afewerki, I. Ibrahem, J. Rydfjord, P. Breistein, A. Córdova, Chem. Eur. J. .2012,18, 2972-2977.

Y. M. Khetmalis, M. Shivani, S. Murugesan, K. V. G. Chandra Sekhar, Biomed. Pharmacother. 2021, 141, 111842.

T.-H. Kang, Y. Murakami, K. Matsumoto, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 2002, 455, 27-34.

H. Guan, A. D. Laird, R. A. Blake, C. Tang, C. Liang, Bioorg. Med. Chem. Lett. 2004, 14, 187-190.

W. Sun, G. Zhu, C. Wu, L. Hong, R. Wang, Chem. Eur. J. 2012, 18, 13959-13963.

L. Deiana, Y. Jiang, C. Palo-Nieto, S. Afewerki, C. A. Incerti-Pradillos, O. Verho, C.-W. Tai, E. V. Johnston, A. Córdova, Angew. Chem. Int. Ed. 2014, 53, 3447-3451;

Angew. Chem. 2014, 126, 3515-3519.

S. Afewerki, G. Ma, I. Ibrahem, L. Liu, J. Sun, A. Córdova, ACS Catal. 2015, 5, 1266-1272.

M. Meazza, R. Rios, Chem. Eur. J. 2016, 22, 9923-9928.

J.-A. Xiao, J.-L. Li, X.-L. Cheng, K. Chen, H. Peng, W.-Q. Chen, W. Su, Y.-M. Huang, H. Yang, Chem. Commun. 2021, 57, 4456-4459.

K. C. Nicolaou, Q. Kang, T. R. Wu, C. S. Lim, D. Y.-K. Chen, J. Am. Chem. Soc. 2010, 132, 7540-7548.

Z.-Y. Cheng, Y.-Q. Du, Q. Zhang, B. Lin, P.-Y. Gao, X.-X. Huang, S.-J. Song, Tetrahedron Lett. 2018, 59, 2050-2053.

Y.-J. Kwon, M.-J. Sohn, C.-J. Zheng, W.-G. Kim, Org. Lett. 2007, 9, 2449-2451.

A. S. Ivanov, Chem. Soc. Rev. 2008, 37, 789-811.

M. Laugeois, S. Ponra, V. Ratovelomanana-Vidal, V. Michelet, M. R. Vitale, Chem. Commun. 2016, 52, 5332-5335.

N. Shafiq, U. Arshad, G. Zarren, S. Parveen, I. Javed, A. Ashraf, Curr. Org. Chem. 2020, 24, 129-161.

N. B. G. Taylor, R. L. Noble, Nature 1949, 163, 447.

X. Bao, X. Wang, J.-M. Tian, X. Ye, B. Wang, H. Wang, Org. Biomol. Chem. 2022, 20, 2370-2386.

B. Formánek, V. Šeferna, M. Meazza, R. Rios, M. Patil, J. Veselý, Eur. J. Org. Chem. 2021, 2021, 2362-2366.

M. Urban, M. Nigríni, I. Císařová, J. Veselý, J. Org. Chem. 2021, 86, 18139-18155.

M. Šimek, M. Remeš, J. Veselý, R. Rios, Asian J. Org. Chem. 2013, 2, 64-68.

M. Kamlar, I. Císařová, J. Veselý, Org. Biomol. Chem. 2015, 13, 2884-2889.

M. Meazza, M. Kamlar, L. Jašíková, B. Formánek, A. Mazzanti, J. Roithová, J. Veselý, R. Rios, Chem. Sci. 2018, 9, 6368-6373.

S. Putatunda, J. V. Alegre-Requena, M. Meazza, M. Franc, D. Rohal'ová, P. Vemuri, I. Císařová, R. P. Herrera, R. Rios, J. Veselý, Chem. Sci. 2019, 10, 4107-4115.

I. F. S. Marra, P. P. de Castro, G. W. Amarante, Eur. J. Org. Chem. 2019, 2019, 5830-5855.

A.-N. R. Alba, R. Rios, Chem. - An Asian J. 2011, 6, 720-734.

J. S. Fisk, R. A. Mosey, J. J. Tepe, Chem. Soc. Rev. 2007, 36, 1432-1440.

M. Kamlar, M. Franc, I. Císařová, R. Gyepes, J. Veselý, Chem. Commun. 2019, 55, 3829-3832.

M. Mahdavi, M. Saeedi, H. Nadri, M. Eghtedari, S. Gholizadeh, R. Hariri, T. Akbarzadeh, Lett. Org. Chem. 2017, 14, 186-191.

D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, L. Zaprutko, A. Gzella, R. Lesyk, Eur. J. Med. Chem. 2009, 44, 1396-1404.

S. Yan, T. Appleby, G. Larson, J. Z. Wu, R. K. Hamatake, Z. Hong, N. Yao, Bioorg. Med. Chem. Lett. 2007, 17, 1991-1995.

M. Franc, I. Císařová, J. Veselý, Adv. Synth. Catal. 2021, 363, 4349-4353.

D. M. Flanigan, F. Romanov-Michailidis, N. A. White, T. Rovis, Chem. Rev. 2015, 115, 9307-9387.

R. S. Menon, A. T. Biju, V. Nair, Chem. Soc. Rev. 2015, 44, 5040-5052.

M. N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 2014, 510, 485-496.

A. Grossmann, D. Enders, Angew. Chem. Int. Ed. 2012, 51, 314-325;

Angew. Chem. 2012, 124, 320-332.

M. H. Wang, K. A. Scheidt, Angew. Chem. Int. Ed. 2016, 55, 14912-14922;

Angew. Chem. 2016, 128, 15134-15145.

M. H. Wang, K. A. Scheidt, Angew. Chem. 2016, 128, 15134-15145;

Angew. Chem. Int. Ed. 2016, 55, 14912-14922.

Z. J. Zhang, L. Zhang, R. L. Geng, J. Song, X. H. Chen, L. Z. Gong, Angew. Chem. Int. Ed. 2019, 58, 12190-12194;

Angew. Chem. 2019, 131, 12318-12322.

Z.-J. Zhang, Y.-H. Wen, J. Song, L.-Z. Gong, Angew. Chem. Int. Ed. 2021, 60, 3268-3276;

Angew. Chem. 2021, 133, 3305-3313.

T. Fan, J. Song, L.-Z. Gong, Angew. Chem. Int. Ed. 2022, 61, e202201678.

D. T. Cohen, K. A. Scheidt, Chem. Sci. 2012, 3, 53-57.

J. Dugal-Tessier, E. A. O'Bryan, T. B. H. Schroeder, D. T. Cohen, K. A. Scheidt, Angew. Chem. Int. Ed. 2012, 51, 4963-4967;

Angew. Chem. 2012, 124, 5047-5051.

D. T. Cohen, B. Cardinal-David, K. A. Scheidt, Angew. Chem. Int. Ed. 2011, 50, 1678-1682;

Angew. Chem. 2011, 123, 1716-1720.

D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766-771.

J. Dugal-Tessier, E. A. O'Bryan, T. B. H. Schroeder, D. T. Cohen, K. A. Scheidt, Angew. Chem. 2012, 124, 5047-5051;

Angew. Chem. Int. Ed. 2012, 51, 4963-4967.

Z. Xiao, C. Yu, T. Li, X.-S. Wang, C. Yao, Org. Lett. 2014, 16, 3632-3635.

W.-Q. Jia, H.-M. Zhang, C.-L. Zhang, Z.-H. Gao, S. Ye, Org. Chem. Front. 2016, 3, 77-81.

R. Maji, S. C. Mallojjala, S. E. Wheeler, Chem. Soc. Rev. 2018, 47, 1142-1158.

S. E. Wheeler, T. J. Seguin, Y. Guan, A. C. Doney, Acc. Chem. Res. 2016, 49, 1061-1069.

R. R. Knowles, E. N. Jacobsen, Proc. Natl. Acad. Sci. USA 2010, 107, 20678-20685.

T. Akiyama, K. Mori, Chem. Rev. 2015, 115, 9277-9306.

D. Kampen, C. M. Reisinger, B. List, in (Ed.: B. List), Springer Berlin Heidelberg, Berlin, Heidelberg, 2009, pp. 1-37.

T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010.

P. B. Neupane, K. G. Friestad, Curr. Org. Chem. 2022, 26, 991-1001.

Y.-D. Shao, D.-J. Cheng, ChemCatChem 2021, 13, 1271-1289.

A. G. Woldegiorgis, X. Lin, Beilstein J. Org. Chem. 2021, 17, 2729-2764.

T. Parvin, R. Yadav, L. H. Choudhury, Org. Biomol. Chem. 2020, 18, 5513-5532.

Y.-L. Sun, Y. Wei, M. Shi, ChemCatChem 2017, 9, 718-727.

Y. Takemoto, Chem. Pharm. Bull. 2010, 58, 593-601.

E. A. Popova, Y. A. Pronina, A. V. Davtian, G. D. Nepochatyi, M. L. Petrov, V. M. Boitsov, A. V. Stepakov, Russ. J. Gen. Chem. 2022, 92, 287-347.

X.-Q. Hou, D.-M. Du, Adv. Synth. Catal. 2020, 362, 4487-4512.

S. Sunny, M. Maingle, K. Seth, Synlett 2022.

G. Xiao, T. Chen, C. Ma, D. Xing, W. Hu, Org. Lett. 2018, 20, 4531-4535.

A. Gopi Krishna Reddy, P. Niharika, S. Zhou, S.-K. Jia, T. Shi, X. Xu, Y. Qian, W. Hu, Org. Lett. 2020, 22, 2925-2930.

J. E. Aho, P. M. Pihko, T. K. Rissa, Chem. Rev. 2005, 105, 4406-4440.

F. Perron, K. F. Albizati, Chem. Rev. 1989, 89, 1617-1661.

H. Wu, Y.-P. He, L.-Z. Gong, Org. Lett. 2013, 15, 460-463.

L. Cala, A. Mendoza, F. J. Fañanás, F. Rodríguez, Chem. Commun. 2013, 49, 2715-2717.

A. A. Rexit, M. Mailikezati, Tetrahedron Lett. 2015, 56, 2651-2655.

G. Li Petri, M. V. Raimondi, V. Spanò, R. Holl, P. Barraja, A. Montalbano, Top. Curr. Chem. 2021, 379, 34.

V. Corti, E. Marcantonio, M. Mamone, A. Giungi, M. Fochi, L. Bernardi, Catalysts 2020, 10, 150.

L. Ye, Y. Tian, X. Meng, Q.-S. Gu, X.-Y. Liu, Angew. Chem. Int. Ed. 2020, 59, 1129-1133;

Angew. Chem. 2020, 132, 1145-1149.

L. S. Schwartzberg, M. R. Modiano, B. L. Rapoport, M. R. Chasen, C. Gridelli, L. Urban, A. Poma, S. Arora, R. M. Navari, I. D. Schnadig, Lancet Oncol. 2015, 16, 1071-1078.

J. Wang, F. Chen, Y. Liu, Y. Liu, K. Li, X. Yang, S. Liu, X. Zhou, J. Yang, J. Nat. Prod. 2018, 81, 2722-2730.

J. Wrobel, A. Dietrich, S. A. Woolson, J. Millen, M. McCaleb, M. C. Harrison, T. C. Hohman, J. Sredy, D. Sullivan, J. Med. Chem. 1992, 35, 4613-4627.

W.-K. Yuan, B.-F. Shi, Angew. Chem. Int. Ed. 2021, 60, 23187-23192;

Angew. Chem. 2021, 133, 23371-23376.

D.-A. Li, X.-H. He, X. Tang, Y. Wu, H. Zhao, G. He, C. Peng, B. Han, G. Zhan, Org. Lett. 2022, 24, 6197-6201.

D. Hack, A. B. Dürr, K. Deckers, P. Chauhan, N. Seling, L. Rübenach, L. Mertens, G. Raabe, F. Schoenebeck, D. Enders, Angew. Chem. 2016, 128, 1829-1832;

Angew. Chem. Int. Ed. 2016, 55, 1797-1800.

Find record

Citation metrics

Loading data ...

Archiving options

Loading data ...