Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring-Opening.
Cyclopropanation
Cyclopropenes
Dearomative
Naphthols
Rhodium catalysis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
14 Feb 2022
14 Feb 2022
Historique:
received:
26
11
2021
pubmed:
24
12
2021
medline:
24
12
2021
entrez:
23
12
2021
Statut:
ppublish
Résumé
The dearomatization of 2-naphthols represents a simple method for the construction of complex 3D structures from simple planar starting materials. We describe a cyclopropanation of 2-naphthols that proceeds via cyclopropene ring-opening using rhodium and acid catalysis under mild conditions. The vinyl cyclopropane molecules were formed with high chemoselectivity and scalability, which could be further functionalized at different sites. Both computational and experimental evidence were used to elucidate the reaction mechanism.
Identifiants
pubmed: 34939302
doi: 10.1002/anie.202116171
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202116171Subventions
Organisme : NSERC (Natural Sciences and Engineering Research Council)
Organisme : University of Toronto
Organisme : Kennarshore
Organisme : NSERC Postgraduate Scholarship Fund
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
M. W. B. McCulloch, R. A. Barrow, Molecules 2005, 10, 1272-1278;
P. Seephonkai, S. G. Pyne, A. C. Willis, W. Lie, J. Nat. Prod. 2013, 76, 1358-1364;
M. C. Kozlowski, E. C. Dugan, E. S. DiVirgilio, K. Maksimenka, G. Bringmann, Adv. Synth. Catal. 2007, 349, 583-594.
J. A. M. Vargas, D. P. Day, A. C. B. Burtoloso, Eur. J. Org. Chem. 2021, 741-756;
T. Takeya, H. Doi, T. Ogata, I. Okamoto, E. Kotani, Tetrahedron 2004, 60, 9049-9060.
Z.-L. Xia, C. Zheng, R.-Q. Xu, S.-L. You, Nat. Commun. 2019, 10, 3150-3156;
J. An, M. Bandini, Eur. J. Org. Chem. 2020, 4087-4097;
K. Kulish, C. Boldrini, M. C. Reis, J. M. Pérez, S. R. Harutyunyan, Chem. Eur. J. 2020, 26, 15843-15846;
H. Homma, S. Harada, T. Ito, A. Kanda, T. Nemoto, Org. Lett. 2020, 22, 8132-8138.
Z. Fu, J. Zhu, S. Guo, A. Lin, Chem. Commun. 2021, 57, 1262-1265;
S.-B. Tang, H.-F. Tu, X. Zhang, S.-L. You, Org. Lett. 2019, 21, 6130-6134;
L. Ding, W.-T. Wu, L. Zhang, S.-L. You, Org. Lett. 2020, 22, 5861-5865;
S.-S. Zhang, J. Xue, Q. Gu, X. Jiang, S.-L. You, Org. Biomol. Chem. 2021, 19, 8761-8771;
B. Yang, X. Zhai, S. Feng, Z. Shao, Org. Chem. Front. 2018, 5, 2794-2798;
L. Bai, X. Luo, Y. Ge, H. Wang, J. Liu, Y. Wang, X. Luan, CCS Chem. 2021, 3, 1155-1165.
J.-C. Yi, H.-F. Tu, S.-L. You, Org. Biomol. Chem. 2018, 16, 8700-8703.
K. Y. Koltunov, Tetrahedron Lett. 2008, 49, 3891-3894;
M. Ue, M. Kinugawa, K. Kakiuchi, Y. Tobe, Y. Odaira, Tetrahedron Lett. 1989, 30, 6193-6194;
K. Kakiuchi, B. Yamaguchi, M. Kinugawa, M. Ue, Y. Tobe, Y. Odaira, J. Org. Chem. 1993, 58, 2797-2803.
For recent reviews on dearomative reactions done by our group and others, see:
N. Zeidan, M. Lautens, Synthesis 2019, 51, 4137-4146;
C. Zheng, S.-L. You, ACS Cent. Sci. 2021, 7, 432-444;
W. C. Wertjes, E. H. Southgate, D. Sarlah, Chem. Soc. Rev. 2018, 47, 7996-8017;
C.-X. Zhuo, W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 12662-12686;
Angew. Chem. 2012, 124, 12834-12858;
W.-T. Wu, L. Zhang, S.-L. You, Chem. Soc. Rev. 2016, 45, 1570-1580;
Q. Ding, Y. Ye, R. Fan, Synthesis 2013, 45, 1-16;
Q. Ding, X. Zhou, R. Fan, Org. Biomol. Chem. 2014, 12, 4807-4815;
U. K. Sharma, P. Ranjan, E. V. Van der Eycken, S.-L. You, Chem. Soc. Rev. 2020, 49, 8721-8748;
C. Jing, J. J. Farndon, J. F. Bower, Chem. Rec. 2021, 21, 2909-2926.
A. de Meijere, Angew. Chem. Int. Ed. Engl. 1979, 18, 809-826;
Angew. Chem. 1979, 91, 867-884;
J. G. Hamilton, W. E. Palke, J. Am. Chem. Soc. 1993, 115, 4159-4164.
For examples of cyclopropanes in biologically active molecules, see:
W. A. Donaldson, Tetrahedron 2001, 57, 8589-8627;
Y.-Y. Fan, X.-H. Gao, J.-M. Yue, Sci. China Chem. 2016, 59, 1126-1141;
D. Y.-K. Chen, R. H. Pouwer, J.-A. Richard, Chem. Soc. Rev. 2012, 41, 4631-4642;
C. Ebner, E. M. Carreira, Chem. Rev. 2017, 117, 11651-11679.
For reviews on cyclopropanation reactions, see:
H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050;
W. Wu, Z. Lin, H. Jiang, Org. Biomol. Chem. 2018, 16, 7315-7329;
M. Brookhart, W. B. Studabaker, Chem. Rev. 1987, 87, 411-432;
“Intermolecular Metal-Catalyzed Carbenoid Cyclopropanations”: H. M. L. Davies, E. G. Antoulinakis in Organic Reactions, Vol. 57 (Ed.: L. E. Overman), Wiley, Hoboken, 2001, pp. 1-326;
“Simmons-Smith Cyclopropanation Reaction”: A. B. Charette, A. Beauchemin in Organic Reactions, Vol. 58 (Ed.: L. E. Overman), Wiley, Hoboken, 2001, pp. 1-415;
L. Dian, I. Marek, Chem. Rev. 2018, 118, 8415-8434;
D. Qian, J. Zhang, Chem. Soc. Rev. 2015, 44, 677-698;
M. Bos, T. Poisson, X. Pannecoucke, A. B. Charette, P. Jubault, Chem. Eur. J. 2017, 23, 4950-4961;
M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179;
A. P. Thankachan, K. S. Sindhu, K. K. Krishnan, G. Anilkumar, Org. Biomol. Chem. 2015, 13, 8780-8802;
H. M. L. Davies, S. J. Hedley, Chem. Soc. Rev. 2007, 36, 1109-1119.
A. Archambeau, F. Miege, C. Meyer, J. Cossy, Acc. Chem. Res. 2015, 48, 1021-1031;
R. Vicente, Chem. Rev. 2021, 121, 162-226;
F. Miege, C. Meyer, J. Cossy, Angew. Chem. Int. Ed. 2011, 50, 5932-5937;
Angew. Chem. 2011, 123, 6054-6059;
R. Vicente, Synthesis 2016, 48, 2343-2360;
J. González, A. de la Fuente, M. J. González, L. D. de Tejada, L. A. López, R. Vicente, Beilstein J. Org. Chem. 2019, 15, 285-290;
P. Guo, W. Sun, Y. Liu, Y.-X. Li, T.-P. Loh, Y. Jiang, Org. Lett. 2020, 22, 5978-5983;
Z.-B. Zhu, Y. Wei, M. Shi, Chem. Soc. Rev. 2011, 40, 5534-5563.
Selected examples:
Y. Guo, T. V. Nguyen, R. M. Koenigs, Org. Lett. 2019, 21, 8814-8818;
R. R. Nani, S. Reisman, J. Am. Chem. Soc. 2013, 135, 7304-7311;
S. Zhao, X.-X. Chen, N. Gao, M. Qian, X. Chen, J. Org. Chem. 2021, 86, 7131-7140;
H. Wang, D. M. Guptill, A. Varela-Alvarez, D. G. Musaev, H. M. L. Davies, Chem. Sci. 2013, 4, 2844-2850;
I. D. Jurberg, H. M. L. Davies, Chem. Sci. 2018, 9, 5112-5118.
D. Zhu, L. Chen, H. Fan, Q. Yao, S. Zhu, Chem. Soc. Rev. 2020, 49, 908-950;
K. Dong, X. Fan, C. Pei, Y. Zheng, S. Chang, J. Cai, L. Qiu, Z.-X. Yu, X. Xu, Nat. Commun. 2020, 11, 2363;
M. Lee, Z. Ren, D. G. Musaev, H. M. L. Davies, ACS Catal. 2020, 10, 6240-6247;
R. Fang, L. Yang, L. Zhou, A. M. Kirillov, L. Yang, Org. Lett. 2020, 22, 4043-4048.
R. J. Ross, R. Jeyaseelan, M. Lautens, Org. Lett. 2020, 22, 4838-4843.
S. Won Youn, C.-G. Cho, Org. Biomol. Chem. 2021, 19, 5028-5047;
C. Empel, S. Jana, C. Pei, T. V. Nguyen, R. M. Koenigs, Org. Lett. 2020, 22, 7225-7229;
Z. Yu, Y. Li, P. Zhang, L. Liu, J. Zhang, Chem. Sci. 2019, 10, 6553-6559;
B. Ma, Z. Tang, J. Zhang, L. Liu, Chem. Commun. 2020, 56, 9485-9488.
S. Harada, C. Sakai, K. Tanikawa, T. Nemoto, Tetrahedron 2019, 75, 3650-3656.
Deposition Numbers 2124602 (for (Z)-3c), 2124604 (for 5) and 2124605 (for 6) 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.
S. K. Alamsetti, M. Spanka, C. Schneider, Angew. Chem. Int. Ed. 2016, 55, 2392-2396;
Angew. Chem. 2016, 128, 2438-2442;
A. Suneja, C. Schneider, Org. Lett. 2018, 20, 7576-7580;
G. Xu, S. Tang, Y. Shao, J. Sun, Chem. Commun. 2019, 55, 9096-9099.