10.1002/anie.201916727
Angewandte Chemie International Edition
COMMUNICATION
[4] Applications of skeletal reorganization in natural product synthesis: a) A.
Saitman, P. Rulliere, S. D. E. Sullivan, E. A. Theodorakis, Org. Lett. 2011,
13, 5854–5857; b) O. Wagnieres, Z. Xu, Q. Wang, J. Zhu, J. Am. Chem.
Soc. 2014, 136, 15102–15108; c) X.-M. Zhang, Y.-Q. Tu, F.-M. Zhang, Z.-
H. Chen, S.-H. Wang, Chem. Soc. Rev. 2017, 46, 2272–2305; d) J. R.
Hanson, J. Chem. Res. 2018, 42, 175–180; e) D. K. Singh, I. Kim, J. Org.
Chem. 2018, 83, 1667–1672.
[5] For leading reviews on oxetane chemistry, see: a) J. A. Burkhard, G.
Wuitschik, M. Rogers-Evans, K. Müller, E. M. Carreira, Angew Chem. Int.
Ed. 2010, 49, 9052‒9067; b) D. J. Mack, J. T. Njardarson, ACS Catal.
2013, 3, 272-286; c) Z. Wang, Z. Chen, J. Sun, Org. Biomol. Chem. 2014,
12, 6028‒6032; d) C. A. Malapit, A. R. Howell, J. Org. Chem. 2015, 80,
8489–8495; e) J. A. Bull, R. A. Croft, O. A. Davis, R. Doran, K. F. Morgan,
Chem. Rev. 2016, 116, 12150–12233.
[6] a) M. Mizuno, M. Kanai, A. Iida, K. Tomioka, Tetrahedron: Asymmetry
1996, 7, 2483‒2484; b) R. N. Loy, E. N. Jacobsen, J. Am. Chem. Soc.
2009, 131, 2786‒2787; c) J. A. Burkhard, B. H. Tchitchanov, E. M.
Carreira, Angew. Chem. Int. Ed. 2011, 50, 5379‒5382; d) S. A. Ruider, S.
Müller, E. M. Carreira, Angew. Chem. Int. Ed. 2013, 52, 11908‒11911; e)
A. R. White, R. A. Kozlowski, S.-C. Tsai, C. D. Vanderwal, Angew. Chem.
Int. Ed. 2017, 56, 10525‒10529; For our own efforts: f) W. Zhao, Z. Wang,
J. Sun, Angew. Chem. Int. Ed. 2012, 51, 6209‒6213; g) Z. Chen, B. Wang,
Z. Wang, G. Zhu, J. Sun, Angew. Chem., Int. Ed. 2013, 52, 2027‒2031; h)
Z. Wang, Z. Chen, J. Sun, Angew. Chem., Int. Ed. 2013, 52, 6685‒6688; i)
W. Yang, J. Sun, Angew. Chem. Int. Ed. 2016, 55, 1868‒1871; j) W. Yang,
Z. Wang, J. Sun, Angew. Chem. Int. Ed. 2016, 55, 6954‒6958; k) R.
Zhang, W. Guo, M. Duan, K. N. Houk, J. Sun, Angew. Chem. Int. Ed. 2019,
58, 18055‒18060; l) H. Huang, W. Yang, Z. Chen, Z. Lai, J. Sun, Chem.
Sci. 2019, 10, 9586‒9590.
Scheme 5. Product transformations. [a] Pd/C, H2, EtOAc, RT. [b] NaOH, EtOH,
100 oC. [c] Tf2O, pyridine, DCM, RT. [d] PhB(OH)2, Pd(PPh3)2Cl2, Cs2CO3, 1,4-
dioxane, H2O, reflux. [e] Mg, Pd/C, NH4OAc, MeOH, RT. [f] mCPBA, DCM, RT.
[g] Na/naphthalene, DME, -50 oC. PG = (p-OMe)C6H4SO2.
Acknowledgements
Financial support was provided by NSFC (21572192, 91956114)
and Hong Kong RGC (16302318) and Jiangsu specially
appointed professors program. We also thank Dr. Dengke Ma
and Dr. Renwei Zhang for helpful discussion and Dr. Herman
Sung for assistance in structural determination.
[7] a) H. Nozaki, S. Moriuti, H. Takaya, R. Noyori, Tetrahedron Lett. 1966, 43,
5239‒5244; b) T.-Y. Y. Gu, W. P. Weber, J. Am. Chem. Soc. 1980, 102,
1641‒1644; c) K. Ito, T. Katsuki, Chem. Lett. 1994, 1857‒1860; d) M. M.-
C. Lo, G. C. Fu, Tetrahedron 2001, 57, 2621‒2634; e) D. Rix, R.
Ballesteros-Garrido, W. Zeghida, C. Besnard, J. Lacour, Angew. Chem. Int.
Ed. 2011, 50, 7308‒7311; f) C. Gronnier, S. Kramer, Y. Odabachian, F.
Gagosz, J. Am. Chem. Soc. 2012, 134, 828‒831; g) B. Guo, G.
Schwarzwalder, J. T. Njardarson, Angew. Chem. Int. Ed. 2012, 51, 5675‒
5678; h) Q. Yin, S.-L. You, Org. Lett. 2014, 16, 1810‒1813; i) J. Rintjema,
W. Guo, E. Martin, E. C. Escudero-Adan, A. W. Kleij, Chem. Eur. J. 2015,
21, 10754‒10762; j) Y.-N. Wang, L.-C. Yang, Z.-Q. Rong, T.-L. Liu, R. Liu,
Y. Zhao, Angew. Chem. Int. Ed. 2018, 57, 1596‒1600; k) H. Xu, S. Khan,
H. Li, X. Wu, Y. J. Zhang, Org. Lett. 2019, 21, 214‒217.
Keywords: strained molecules • nitrogen heterocycles •
rearrangement • oxetane • cyclization
[1] a) “Skeletal Rearrangement Reactions”: I. Nakamura in Transition-Metal-
Mediated Aromatic Ring Construction (Ed.: K. Tanaka), Wiley, New Jersey,
2013, pp. 743–771; b) X. Xie, L. Zu, Synlett 2018, 29, 1008-1013.
[2] Selected reviews (a–c) and examples (d–l) on skeletal reorganization of
alkynes, such as enyne cycloisomerization: a) C. Aubert, O. Buisine, M.
Malacria, Chem. Rev. 2002, 102, 813–834; b) L. Zhang, J. Sun, S. A.
Kozmin, Adv. Synth. Catal. 2006, 348, 2271–2296; c) M. Tobisu, N.
Chatani, Chem. Soc. Rev. 2008, 37, 300–307; d) N. Chatani, H. Inoue, T.
Kotsuma, S. Murai, J. Am. Chem. Soc. 2002, 124, 10294–10295; e) V.
Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126,
8654–8655; f) G. Zhang, V. J. Catalano, L. Zhang, J. Am. Chem. Soc.
2007, 129, 11358–11359; g) J.-M. Tang, S. Bhunia, S. M. A. Sohel, M.-Y.
Lin, H.-Y. Liao, S. Datta, A. Das, R.-S. Liu, J. Am. Chem. Soc. 2007, 129,
15677–15683; h) K. Ota, S. I. Lee, J.-M. Tang, M. Takachi, H. Nakai, T.
Morimoto, H. Sakurai, K. Kataoka, N. Chatani, J. Am. Chem. Soc. 2009,
132, 15203–15211; i) I. Nakamura, D. Zhang, M. Terada, J. Am. Chem.
Soc. 2010, 132, 7884–7886; j) J. Barluenga, E. T.udela, R. Vicente, A.
Ballesteros, M. Tomás, Angew. Chem. Int. Ed. 2011, 50, 2107–2110; k) T.
Matsuda, T. Goya, L. Liu, Y. Sakurai, S. Watanuki, N. Ishida, M. Murakami,
Angew. Chem. Int. Ed. 2013, 52, 6492–6495; l) B. Zhou, L. Li, X.-Q. Zhu,
J.-Z. Yan, Y.-L. Guo, L.-W. Ye, Angew. Chem. Int. Ed. 2017, 56, 4015–
4019.
[8] a) L. M. Nainwal, M. M. Alam, Eur. J. Med. Chem. 2019, 164, 121‒170; b)
N. J. Victor, R. Sakthivel, K. M. Muraleedharan, D. Karunagaran,
ChemMedChem, 2013, 8, 1623‒1628; c) S. Duggirala, J. V. Napoleon, R.
P. Nankar, V. S. Adeeba, M. K. Manheri, M. Doble, Eur. J. Med. Chem.
2016, 123, 557‒567; d) H. Takahashi, Y. Bekkali, A. J. Capolino, T.
Gilmore, S. E. Goldrick, R. M. Nelson, D. Trenzio, J. Wang, L. Zuvela-
Jelaska, J. Proudfoot, G. Nabozny, D. Thomson, Bioorg. Med. Chem. Lett.
2006, 16, 1549‒1552.
[9] For selected other methods for the synthesis of 1,2-dihydroquinolines: a) Y.
Luo, Z. Li, C.-J. Li, Org. Lett. 2005, 7, 2675‒2678; b) X. Liu, Y. Liu, Org.
Biomol. Chem. 2010, 8, 4063‒4065; c) C. Zhu, S. Ma, Angew. Chem. Int.
Ed. 2014, 53, 13532‒13535; d) D, Ding, T. Mou, M. Feng, X. Jiang, J. Am.
Chem. Soc. 2016, 138, 5218‒5221; e) R. Kuppusamy, R. Santhoshkumar,
R. Boobalan, H.-R. Wu, C.-H. Cheng, ACS Catal. 2018, 8, 1880‒1883.
[10]a) H. O. House, J. Am. Chem. Soc. 1955, 77, 3070‒3075; b) J. Meinwald,
S. S. Labana, M. S. Chadha, J. Am. Chem. Soc. 1963, 85, 582‒585.
[3] Selected examples on skeletal reorganization of other functionalities: a) d)
T.-P. Loh, Q.-Y. Hu, K.-T. Tan, H.-S. Cheng, Org. Lett. 2001, 3, 2669–
2672; b) J. M. Ndungu, K. L. Larson, R. Sarpong, Org. Lett. 2005, 7,
5845–5848; c) S. Álvarez, G. Domínguez, A. Gradillas, J. Pérez-Castells,
Eur. J. Org. Chem. 2013, 3094–3102; d) H. Zhang, C. Li, G. Xie, B. Wang,
Y. Zhang, J. Wang, J. Org. Chem. 2014, 79, 6286–6293; e) N. Wang, Q.-S.
Gu, Z.-L. Li, Z. Li, Y.-L. Guo, Z. Guo, X.-Y. Liu, Angew. Chem. Int. Ed.
2018, 57, 14225–14229.
4
This article is protected by copyright. All rights reserved.