Chalcogen Bonding Catalysis of the Cloke-Wilson Rearrangement.
Cloke-Wilson rearrangement
Se⋅⋅⋅O bonding
chalcogen bonding
cyclopropanes
supramolecular catalysis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
08 May 2023
08 May 2023
Historique:
received:
07
12
2022
medline:
18
2
2023
pubmed:
18
2
2023
entrez:
17
2
2023
Statut:
ppublish
Résumé
The Cloke-Wilson rearrangement is an important method to construct heterocycles which was conventionally facilitated by strong Lewis acids, Brønsted acids and Lewis bases. A weak interaction catalysis approach to the Cloke-Wilson rearrangement remains a challenging topic and yet no example is reported. Herein, a chalcogen bonding catalysis method to achieve the Cloke-Wilson rearrangement is described that involves activation of carbonyl cyclopropanes by double Se⋅⋅⋅O interactions. This chalcogen bonding catalysis approach afforded a wide range of dihydrofurans with good yields, thus establishing an alternative strategy to catalyze the Cloke-Wilson rearrangement.
Identifiants
pubmed: 36799517
doi: 10.1002/chem.202203822
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203822Subventions
Organisme : National Natural Science Foundation of China
ID : 22022105, 21971147, 21772113
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
J. B. Cloke, J. Am. Chem. Soc. 1929, 51, 1174-1187.
C. L. Wilson, J. Am. Chem. Soc. 1947, 69, 3002-3004.
V. K. Yadav, R. Balamurugan, Org. Lett. 2001, 3, 2717-2719.
R. K. Bowman, J. S. Johnson, Org. Lett. 2006, 8, 573-576.
Z. Zhang, Q. Zhang, S. Sun, T. Xiong, Q. Liu, Angew. Chem. Int. Ed. 2007, 46, 1726-1729;
Angew. Chem. 2007, 119, 1756-1759.
M. Li, S. Lin, Z. Dong, X. Zhang, F. Liang, J. Zhang, Org. Lett. 2013, 15, 3978-3981.
C.-H. Lin, D. Pursley, J. E. M. N. Klein, J. Teske, J. A. Allen, F. Rami, A. Köhn, B. Plietker, Chem. Sci. 2015, 6, 7034-7043.
J. Zhang, Y. Tang, W. Wei, Y. Wu, Y. Li, J. Zhang, Y. Zheng, S. Xu, Org. Lett. 2017, 19, 3043-3046.
A. Ortega, R. Manzano, U. Uria, L. Carrillo, E. Reyes, T. Tejero, P. Merino, J. L. Vicario, Angew. Chem. Int. Ed. 2018, 57, 8225-8229;
Angew. Chem. 2018, 130, 8357-8361.
T. Li, D. Yan, C. Cui, X. Song, J. Chang, Org. Chem. Front. 2020, 7, 2682-2688.
C. B. Aakeroy, D. L. Bryce, G. R. Desiraju, A. Frontera, A. C. Legon, F. Nicotra, K. Rissanen, S. Scheiner, G. Terraneo, P. Metrangolo, G. Resnati, Pure Appl. Chem. 2019, 91, 1889-1892.
L. Vogel, P. Wonner, S. M. Huber, Angew. Chem. Int. Ed. 2019, 58, 1880-1891;
Angew. Chem. 2019, 131, 1896-1907.
A. Bauzá, T. J. Mooibroek, A. Frontera, ChemPhysChem 2015, 16, 2496-2517.
T. N. Guru Row, R. Parthasarathy, J. Am. Chem. Soc. 1981, 103, 477-479.
J. Lu, Y. Lu, S. Yang, W. Zhu, Struct. Chem. 2011, 22, 757-763.
R. E. Rosenfield, R. Parthasarathy, J. D. Dunitz, J. Am. Chem. Soc. 1977, 99, 4860-4862.
M. Iwaoka, S. Takemoto, S. Tomoda, J. Am. Chem. Soc. 2002, 124, 10613-10620.
P. Politzer, J. S. Murray, T. Clark, Phys. Chem. Chem. Phys. 2013,15, 11178-11189.
B. R. Beno, K. S. Yeung, M. D. Bartberger, L. D. Pennington, N. A. Meanwell, J. Med. Chem. 2015, 58, 4383-4438.
M. Fourmigué, A. Dhaka, Coord. Chem. Rev. 2020, 403, 213084.
V. B. Birman, X. Li, Z. Han, Org. Lett. 2007, 9, 37-40.
C. A. Leverett, V. C. Purohit, D. Romo, Angew. Chem. Int. Ed. 2010, 49, 9479-9483;
Angew. Chem. 2010, 122, 9669-9673.
E. R. T. Robinson, C. Fallan, C. Simal, A. M. Z. Slawin, A. D. Smith, Chem. Sci. 2013, 4, 2193-2200.
E. R. T. Robinson, D. M. Walden, C. Fallan, M. D. Greenhalgh, P. H.-Y. Cheong, A. D. Smith, Chem. Sci. 2016, 7, 6919-6927.
C. M. Young, A. Elmi, D. J. Pascoe, R. K. Morris, C. McLaughlin, A. M. Woods, A. B. Frost, A. de la Houpliere, K. B. Ling, T. K. Smith, A. M. Z. Slawin, P. H. Willoughby, S. L. Cockroft, A. D. Smith, Angew. Chem. Int. Ed. 2020, 59, 3705-3710;
Angew. Chem. 2020, 132, 3734-3739.
Y. Abdelhamid, K. Kasten, J. Dunne, W. C. Hartley, C. M. Young, D. B. Cordes, A. M. Z. Slawin, S. Ng, A. D. Smith, Org. Lett. 2022, 24, 5444-5449.
Y. Wang, C. M. Young, H. Liu, W. C. Hartley, M. Wienhold, D. B. Cordes, A. M. Z. Slawin, A. D. Smith, Angew. Chem. Int. Ed. 2022, 61, e202208800.
J. Bitai, A. J. Nimmo, A. M. Z. Slawin, A. D. Smith, Angew. Chem. Int. Ed. 2022, 61, e202202621.
H. Zhao, F. P. Gabbaï, Nat. Chem. 2010, 2, 984-990.
G. E. Garrett, G. L. Gibson, R. N. Straus, D. S. Seferos, M. S. Taylor, J. Am. Chem. Soc. 2015, 137, 4126-4133.
G. E. Garrett, E. I. Carrera, D. S. Seferos, M. S. Taylor, Chem. Commun. 2016, 52, 9881-9884.
J. Y. C. Lim, I. Marques, A. L. Thompson, K. E. Christensen, V. Félix, P. D. Beer, J. Am. Chem. Soc. 2017, 139, 3122-3133.
A. Borissov, I. Marques, J. Y. C. Lim, V. Félix, M. D. Smith, P. D. Beer, J. Am. Chem. Soc. 2019, 141, 4119-4129.
S. Benz, M. Macchione, Q. Verolet, J. Mareda, N. Sakai, S. Matile, J. Am. Chem. Soc. 2016, 138, 9093-9096.
M. Macchione, M. Tsemperouli, A. Goujon, A. R. Mallia, N. Sakai, K. Sugihara, S. Matile, Helv. Chim. Acta. 2018, 101, e1800014.
L. M. Lee, M. Tsemperouli, A. I. Poblador-Bahamonde, S. Benz, N. Sakai, K. Sugihara, S. Matile J. Am. Chem. Soc. 2019, 141, 810-814.
S. Benz, J. López-Andarias, J. Mareda, N. Sakai, S. Matile, Angew. Chem. Int. Ed. 2017, 56, 812-815;
Angew. Chem. 2017, 129, 830-833.
S. Benz, J. Mareda, C. Besnard, N. Sakai, S. Matile, Chem. Sci. 2017, 8, 8164-8169.
P. Wonner, L. Vogel, M. Düser, L. Gomes, F. Kniep, B. Mallick, D. B. Werz, S. M. Huber, Angew. Chem. Int. Ed. 2017, 56, 12009-12012;
Angew. Chem. 2017, 129, 12172-12176.
P. Wonner, A. Dreger, L. Vogel, E. Engelage, S. M. Huber, Angew. Chem. Int. Ed. 2019, 58, 16923-16927;
Angew. Chem. 2019, 131, 17079-17083.
P. Wonner, T. Steinke, L. Vogel, S. M. Huber, Chem. Eur. J. 2020, 26, 1258-1262.
T. Steinke, P. Wonner, R. M. Gauld, S. Heinrich, S. M. Huber, Chem. Eur. J. 2022, 28, e202200917.
W. Wang, H. Zhu, S. Liu, Z. Zhao, L. Zhang, J. Hao, Y. Wang, J. Am. Chem. Soc. 2019, 141, 9175-9179.
W. Wang, H. Zhu, L. Feng, Q. Yu, J. Hao, R. Zhu, Y. Wang, J. Am. Chem. Soc. 2020, 142, 3117-3124.
L. Bao, X. Kong, Y. Wang, Asian J. Org. Chem. 2020, 9, 757-760.
X. Kong, P. Zhou, Y. Wang, Angew. Chem. Int. Ed. 2021, 60, 9395-9400;
Angew. Chem. 2021, 133, 9481-9486.
H. Zhu, P.-P. Zhou, Y. Wang, Nat. Commun. 2022, 13, 3563.
Q. Tong, Z. Zhao, Y. Wang, Beilstein J. Org. Chem. 2022, 18, 325-330.
X. Yuan, Y. Wang, Angew. Chem. Int. Ed. 2022, 61, e202203671.
P. W. N. M. van Leeuwen, M. Raynal, Supramolecular Catalysis: New Directions and Developments, Wiley-VCH, 2022.
M. Breugst, J. J. Koenig, Eur. J. Org. Chem. 2020, 5473-5487.
J. Bamberger, F. Ostler, O. G. Mancheño, ChemCatChem 2019, 11, 5198-5211.
A. Frontera, A. Bauza, Int. J. Mol. Sci. 2021, 22, 12550.
W. Yan, M. Zheng, C. Xu, F.-E. Chen, Green Synth. Catal. 2021, 2, 329-336.