Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone.
1,3-dipole
chiral phosphoric acids
enantioselectivity
higher-order cycloadditions
tropone
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
01 Dec 2020
01 Dec 2020
Historique:
received:
16
07
2020
pubmed:
18
7
2020
medline:
18
7
2020
entrez:
18
7
2020
Statut:
ppublish
Résumé
A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.
Identifiants
pubmed: 32677710
doi: 10.1002/chem.202003329
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15491-15496Subventions
Organisme : Villum Fonden (DK)
ID : 25867
Organisme : Carlsbergfonden
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
J. H. Rigby, Cycloaddition Reactions in Organic Synthesis: Stereoselective Preparation of 7- to 10-membered Ring Systems, Wiley-VCH, Weinheim, 2008;
D. McLeod, M. K. Thøgersen, N. I. Jessen, K. A. Jørgensen, C. S. Jamieson, X.-S. Xue, K. N. Houk, F. Liu, R. Hoffmann, Acc. Chem. Res. 2019, 52, 3488-3501;
S. Frankowski, M. Romaniszyn, A. Skrzyńska, Ł. Albrecht, Chem. Eur. J. 2020, 26, 2120-2132.
Y. Hayashi, H. Gotoh, M. Honma, K. Sankar, I. Kumar, H. Ishikawa, K. Konno, H. Yui, S. Tsuzuki, T. Uchimaru, J. Am. Chem. Soc. 2011, 133, 20175-20185;
Z. Zhou, Z.-X. Wang, Y.-C. Zhou, W. Xiao, Q. Ouyang, W. Du, Y.-C. Chen, Nat. Chem. 2017, 9, 590-594;
S. Wang, C. Rodríguez-Escrich, M. A. Pericàs, Angew. Chem. Int. Ed. 2017, 56, 15068-15072;
Angew. Chem. 2017, 129, 15264-15268;
R. Mose, G. Preegel, J. Larsen, S. Jakobsen, E. H. Iversen, K. A. Jørgensen, Nat. Chem. 2017, 9, 487-492; for related contributions see:
T. A. Palazzo, R. Mose, K. A. Jørgensen, Angew. Chem. Int. Ed. 2017, 56, 10033-10038;
Angew. Chem. 2017, 129, 10165-10171;
T. A. Palazzo, K. A. Jørgensen, Tetrahedron 2018, 74, 7381-7387;
P. Yu, C. Q. He, A. Simon, W. Li, R. Mose, M. K. Thøgersen, K. A. Jørgensen, K. N. Houk, J. Am. Chem. Soc. 2018, 140, 13726-13735.
I. Kallweit, C. Schneider, Org. Lett. 2019, 21, 519-523;
K. Balanna, K. Madica, S. Mukherjee, A. Ghosh, T. Poisson, T. Besset, G. Jindal, A. T. Biju, Chem. Eur. J. 2020, 26, 818-822.
G. Bertuzzi, M. K. Thøgersen, M. Giardinetti, A. Vidal-Albalat, A. Simon, K. N. Houk, K. A. Jørgensen, J. Am. Chem. Soc. 2019, 141, 3288-3297;
D. McLeod, A. Cherubini-Celli, N. Sivasothirajah, C. H. McCulley, M. L. Christensen, K. A. Jørgensen, Chem. Eur. J. 2020, 26, 11417-11422.
B. S. Donslund, A. Monleón, T. A. Palazzo, M. L. Christensen, A. Dahlgaard, J. D. Erickson, K. A. Jørgensen, Angew. Chem. Int. Ed. 2018, 57, 1246-1250;
Angew. Chem. 2018, 130, 1260-1264;
Z. Gao, C. Wang, L. Zhou, C. Yuan, Y. Xiao, H. Guo, Org. Lett. 2018, 20, 4302-4305;
S. Wang, C. Rodríguez-Escrich, M. Finachini, F. Maseras, M. A. Pericàs, Org. Lett. 2019, 21, 3187-3192;
C. He, Z. Li, H. Zhou, J. Xu, Org. Lett. 2019, 21, 8022-8026;
S. Frankowski, A. Skrzyńska, Ł. Albrecht, Chem. Commun. 2019, 55, 11675-11678;
R. Manzano, A. Romaniega, L. Prieto, E. Díaz, E. Reyes, U. Uria, L. Carrillo, J. L. Vicario, Org. Lett. 2020, 22, 4721-4725.
Y. Yang, Y. Jiang, W. Du, Y.-C. Chen, Chem. Eur. J. 2020, 26, 1754-1758;
Y. Liu, G. Luo, X. Yang, S. Jiang, W. Xue, Y. R. Chi, Z. Jin, Angew. Chem. Int. Ed. 2020, 59, 442-448;
Angew. Chem. 2020, 132, 450-456.
B. S. Donslund, N. I. Jessen, G. Bertuzzi, M. Giardinetti, T. A. Palazzo, M. L. Christensen, K. A. Jørgensen, Angew. Chem. Int. Ed. 2018, 57, 13182-13186;
Angew. Chem. 2018, 130, 13366-13370.
V. Nair, K. G. Abhilash, Synlett 2008, 301-312 and references therein.
For non-enantioselective examples see:
Y. Wu, H. Liu, L. Zhang, Z. Sun, Y. Xiao, J. Huang, M. Wang, H. Guo, RSC Adv. 2016, 6, 73547-73550;
T. Roy, A. Jacob, S. Bhattacharjee, A. T. Biju, Chem. Asian J. 2019, 14, 4748-4753;
H. Liu, H. Jia, W. Shi, C. Wang, C. Zhang, H. Guo, Org. Lett. 2018, 20, 3570-3573.
H. Liu, Y. Wu, Y. Zhao, Z. Li, L. Zhang, W. Yang, H. Jiang, C. Jing, H. Yu, B. Wang, Y. Xiao, H. Guo, J. Am. Chem. Soc. 2014, 136, 2625-2629;
H.-L. Teng, L. Yao, C.-J. Wang, J. Am. Chem. Soc. 2014, 136, 4075-4080.
J. Zhang, W. Xiao, H. Hu, L. Lin, X. Liu, X. Feng, Chem. Eur. J. 2018, 24, 13428-13431.
R. Tejero, A. Ponce, J. Adrio, J. C. Carretero, Chem. Commun. 2013, 49, 10406-10408.
B. M. Trost, B. J. McDougall, O. Hartmann, P. T. Wathen, J. Am. Chem. Soc. 2008, 130, 14960-14961;
B. M. Trost, B. J. McDougall, Org. Lett. 2009, 11, 3782-3785.
For selected reviews see:
J. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6784-6794;
J. Adrio, J. C. Carretero, Chem. Commun. 2014, 50, 12434-12446;
J. Adrio, J. C. Carretero, Chem. Commun. 2019, 55, 11979-11991;
L. Wei, X. Chang, C.-J. Wang, Acc. Chem. Res. 2020, 53, 1084-1100.
For selected aminocatalytic examples see:
J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. Int. Ed. 2007, 46, 5168-5170;
Angew. Chem. 2007, 119, 5260-5262;
S. Lin, L. Deiana, G.-L. Zhao, J. Sun, A. Córdova, Angew. Chem. Int. Ed. 2011, 50, 7624-7630;
Angew. Chem. 2011, 123, 7766-7772;
A. Fraile, D. M. Scarpino Schietroma, A. Albrecht, R. L. Davis, K. A. Jørgensen, Chem. Eur. J. 2012, 18, 2773-2776. For selected bifunctional base-catalyzed examples see:
Y.-K. Liu, H. Liu, W. Du, L. Yue, Y.-C. Chen, Chem. Eur. J. 2008, 14, 9873-9877;
L. Tian, G.-Q. Xu, Y.-H. Li, Y.-M. Liang, P.-F. Xu, Chem. Commun. 2014, 50, 2428-2430;
L. Wang, X.-M. Shi, W.-P. Dong, L.-P. Zhu, R. Wang, Chem. Commun. 2013, 49, 3458-3460;
H.-W. Zhao, Z. Yang, W. Meng, T. Tian, B. Li, X.-Q. Song, X.-Q. Chen, H.-L. Pang, Adv. Synth. Catal. 2015, 357, 2492-2502;
V. H. Lauridsen, L. Ibsen, J. Blom, K. A. Jørgensen, Chem. Eur. J. 2016, 22, 3259-3263;
F. Esteban, W. Cieślik, E. M. Arpa, A. Guerrero-Colella, S. Díaz-Tendero, J. Perles, J. A. Fernàndez-Salas, A. Fraile, J. Alemán, ACS Catal. 2018, 8, 1884-1890.
For metal-catalyzed (6+3)-cycloadditions with cycloheptatrienes see:
Q.-H. Li, L. Wei, C.-J. Wang, J. Am. Chem. Soc. 2014, 136, 8685-8692;
Z.-L. He, F. K. Sheong, Q.-H. Li, Z. Lin, C.-J. Wang, Org. Lett. 2015, 17, 1365-1368. For metal-catalyzed (6+3)-cycloadditions with fulvenes see:
M. Potowski, J. O. Bauer, C. Strohmann, A. P. Antonchick, H. Waldmann, Angew. Chem. Int. Ed. 2012, 51, 9512-9516;
Angew. Chem. 2012, 124, 9650-9654;
Z.-L. He, H.-L. Teng, C.-J. Wang, Angew. Chem. Int. Ed. 2013, 52, 2934-2938;
Angew. Chem. 2013, 125, 3006-3010;
M. Potowski, A. P. Antonchick, H. Waldmann, Chem. Commun. 2013, 49, 7800-7802. For metal-catalyzed (6+3)-cycloadditions with tropone see reference 10 and 9a.
For selected examples see:
X.-H. Chen, W.-Q. Zhang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 5652-5653;
J. Yu, L. He, X.-H. Chen, J. Song, W.-J. Chen, L.-Z. Gong, Org. Lett. 2009, 11, 4946-4949;
X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 13819-13825;
J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156-1171;
L. He, X.-H. Chen, D.-N. Wang, S.-W. Luo, W.-Q. Zhang, J. Yu, L. Ren, L.-Z. Gong, J. Am. Chem. Soc. 2011, 133, 13504-13518;
M.-N. Cheng, H. Wang, L.-Z. Gong, Org. Lett. 2011, 13, 2418-2421;
F. Shi, Z.-L. Tao, S.-W. Luo, S.-J. Tu, L.-Z. Gong, Chem. Eur. J. 2012, 18, 6885-6894;
G. Zhu, S. Wu, X. Bao, L. Cui, Y. Zhang, J. Qu, H. Chen, B. Wang, Chem. Commun. 2017, 53, 4714-4717.
While 1,3-dipolar cycloadditions are typically classified according to rules outlined by Rolf Huisgen (Angew. Chem. Int. Ed. Engl. 1968, 7, 321-328;
Angew. Chem. 1968, 80, 329-337), using the number of atoms involved (e.g. (6+3) cycloadditions), IUPAC recommends using the number of electrons involved (e.g. [6+4] cycloadditions). In the introduction, referring to previously reported examples, the nomenclature proposed by the original authors has been used.
T. Nishimura, A. K. Unni, S. Yokoshima, T. Fukuyama, J. Am. Chem. Soc. 2011, 133, 418-419;
T. Nishimura, A. K. Unni, S. Yokoshima, T. Fukuyama, J. Am. Chem. Soc. 2013, 135, 3243-3247;
A. S. Lee, B. B. Liau, M. D. Shair, J. Am. Chem. Soc. 2014, 136, 13442-13452;
J. Zhang, Y. Yan, R. Hu, T. Li, W.-J. Bai, Y. Yang, Angew. Chem. Int. Ed. 2020, 59, 2860-2866;
Angew. Chem. 2020, 132, 2882-2888.
R. B. Ruggeri, M. M. Hansen, C. H. Heathcock, J. Am. Chem. Soc. 1988, 110, 8734-8736;
C. H. Heathcock, M. M. Hansen, R. B. Ruggeri, J. C. Kath, J. Org. Chem. 1992, 57, 2544-2553;
Y. Zhang, Y. Di, H. He, S. Li, Y. Lu, N. Gong, X. Hao, Eur. J. Org. Chem. 2011, 4103-4107;
G. Bélanger, J. Boudreault, F. Lévesque, Org. Lett. 2011, 13, 6204-6207.
B. B. Liau, M. D. Shair, J. Am. Chem. Soc. 2010, 132, 9594-9595;
A. Burtea, J. DeForest, X. Li, S. D. Rychnovsky, Angew. Chem. Int. Ed. 2019, 58, 16193-16197;
Angew. Chem. 2019, 131, 16339-16343.
Methacrolein and simple cinnamaldehyde could not be productively engaged in the desired cycloaddition. The majority of aliphatic aldehydes, with the exception of the aforementioned 1 l, failed to undergo the desired 1,3-dipolar [6+4] cycloaddition, probably due to an overreactive imine I. N-Methylisatin and cyclohexylcarboxaldehyde gave sluggish reactions, where traces of products could be isolated, after heating at 60 °C. However, the results were not satisfactory enough to pursue any further (see Supporting Information).
Substrates 2 having electron-withdrawing groups other than esters, as well as other electron-poor heptafulvenes 3 did not show sufficient reactivity (see Supporting Information).
Deposition Numbers 2013166 contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures..
R. J. Hunadi, G. K. Helmkamp, J. Org. Chem. 1981, 46, 2880-2884;
S. J. Touchette, E. M. Dunkley, L. L. Lowder, J. Wu, Chem. Sci. 2019, 10, 7812-7815.