10.1002/adsc.201801436
Advanced Synthesis & Catalysis
A. A. Zeifman, F. N. Novikov, I. S. Bushmarinov, O. V.
Stroganov, I. Y. Titov, G. G. Chilov, I. V. Svitanko, J.
Am. Chem. Soc. 2017, 139, 3942-3945.
In summary, we have developed an efficient
synthesis of biologically active products via a metal-
free thermal reversible DHDA process. This reaction
features broad substrate scope with various
substituted alkenes, and excellent endo selectivity and
good to excellent yields. In addition, the practical
transformations of the tetrahydroisoindolinones
reveal the potential utility of the new reaction.
Further investigations on the development of new
DHDA reactions are underway in our laboratory.
[4] a) H. Miyamoto, T. Kimura, N. Daikawa, K. Tanaka,
Green Chem. 2003, 5, 57-59; b) S. Takebayashi, J. M.
John, S. H. Bergens, J. Am. Chem. Soc. 2010, 132,
12832-12834; c) R. Cabrero-Antonino Jose, I. Sorribes,
K. Junge, M. Beller, Angew. Chem. Int. Ed. 2015, 128,
395-399.
[5] a) T. Lübbers, P. Angehrn, H. Gmünder, S. Herzig,
Bioorg. Med. Chem. 2007, 17, 4708-4714; b) S. Das, D.
Addis, R. Knöpke Leif, U. Bentrup, K. Junge, A.
Brückner, M. Beller, Angew. Chem. Int. Ed. 2011, 50,
9180-9184.
Experimental Section
General procedure for synthesis of
tetrahydroisoindolinone derivatives.
[6] a) C.-B. Yeh, P.-Y. Lin, J.-M. Hwang, C.-J. Su, Y.-T.
Yeh, S.-F. Yang, M.-C. Chou, Med. Chem. Res. 2012,
21, 953-963; b) K. Indukuri, R. Unnava, M. J. Deka, A.
K. Saikia, J. Org. Chem. 2013, 78, 10629-10641.
In a dry Schlenk tube, a mixture of substituted alkenes 1
(0.4 mmol), maleimides 2 (0.2 mmol) and DDQ (0.3
mmol) in PhCl (2 mL), was stirred at 110 C until the
maleimides 2 was disappeared nearly (monitored by TLC
analysis, about 60 h). After removed the solvent under
reduced pressure, the residue was purified by column
chromatography on silica gel to afford the desired product.
[7] a) K. Ďulák, F. Jonáš, J. Chromatogr. A 1987, 396,
433-436; b) R. Rastogi, S. Gupta, N. Tarannum, R.
Agarwal, R. J. Butcher, Phosphorus, Sulfur, and
Silicon 2017, 192, 300-306.
[8] a) W. Adam, J. Glaeser, K. Peters, M. Prein, J. Am.
Chem. Soc. 1995, 117, 9190-9193; b) F. Fringuelli, R.
Girotti, F. Pizzo, L. Vaccaro, Org. Lett. 2006, 8, 2487-
2489; c) R. R. Pidaparthi, M. E. Welker, C. S. Day, M.
W. Wright, Org. Lett. 2007, 9, 1623-1626; d) J. Mo, S.
H. Kim, P. H. Lee, Org. Lett. 2010, 12, 424-427; e) S.
Mukherjee, E. J. Corey, Org. Lett. 2010, 12, 632-635; f)
C.-M. Ting, Y.-L. Hsu, R.-S. Liu, Chem. Commun.
2012, 48, 6577-6579; g) L. Wang, M. E. Welker, J.
Organomet. Chem. 2013, 723, 15-18; h) K. Tanaka, S.
Nagase, T. Anami, M. Wierzbicki, Z. Urbanczyk-
Lipkowska, RSC Advances 2016, 6, 111436-111439.
Acknowledgements
We thank the National Natural Science Foundation of
China (NSFC-21672170), the Natural Science Basic
Research Plan in Shaanxi Province of China (2018JC-020,
2018JM2029), China Postdoctoral Science Foundation
(2018M643705), the Key Science and Technology
Innovation Team of Shaanxi Province (2017KCT-37) and
the “Top-rated Discipline” Construction Scheme of Shaanxi
Higher Education for financial support.
[9] a) L. Ackermann, R. Vicente, R. Kapdi Anant Angew.
Chem. Int. Ed. 2009, 48, 9792-9826; b) C.-J. Li, Acc.
Chem. Res. 2009, 42, 335-344; c) J. A. Ashenhurst,
Chem. Soc. Rev. 2010, 39, 540-548; d) J. Scheuermann
Caroline Chem. Asian J. 2010, 5, 436-451; e) J. Le
Bras, J. Muzart, Chem. Rev. 2011, 111, 1170-1214; f) C.
Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111,
1780-1824; g) C. S. Yeung, V. M. Dong, Chem. Rev.
2011, 111, 1215-1292; h) A. Batra, P. Singh, N. Singh
Kamal, Eur. J. Org. Chem. 2016, 2016, 4927-4947; i)
Q. Li, W. Hu, R. Hu, H. Lu, G. Li, Org. Lett. 2017, 19,
4676-4679.
References
[1] a) D. J. Newman, G. M. Cragg, J. Nat. Prod. 2007, 70,
461-477;b) K. Kumar, H. Waldmann, Angew. Chem.
Int. Ed. 2009, 48, 3224-3242;c) P. Va, E. L. Campbell,
W. M. Robertson, D. L. Boger, J. Am. Chem. Soc. 2010,
132, 8489-8495;d) S. B. Jones, B. Simmons, A.
Mastracchio, D. W. C. MacMillan, Nature 2011, 475,
183-188.
[2] a) L. Zhou, B. Xu, J. Zhang, Angew. Chem. Int. Ed.
2015, 127, 9220-9224; b) X. Wu, H.-J. Zhu, S.-B. Zhao,
S.-S. Chen, Y.-F. Luo, Y.-G. Li, Org. Lett. 2018, 20,
32-35.
[10] a) E. M. Stang, M. C. White, J. Am. Chem. Soc. 2011,
133, 14892-14895; b) C. Qi, H. Cong, J. Cahill
Katharine, P. Müller, P. Johnson Richard, A. Porco
John, Angew. Chem. Int. Ed. 2013, 52, 8345-8348; c) H.
X. Feng, Y. Y. Wang, J. Chen, L. Zhou, Adv. Synth.
Catal. 2015, 357, 940-944; d) W. Li, L. Zhou, J. Zhang,
Chem. – Eur. J. 2015, 22, 1558-1571; e) C.-W. Kuo, A.
Konala, L. Lin, T.-T. Chiang, C.-Y. Huang, T.-H. Yang,
V. Kavala, C.-F. Yao, Chem. Commun. 2016, 52, 7870-
7873; f) S. Manna, P. Antonchick Andrey, Chem. –Eur.
J. 2017, 23, 7825-7829; g) B. Jiang, Q.-J. Liang, Y.
Han, M. Zhao, Y.-H. Xu, T.-P. Loh, Org. Lett. 2018, 20,
3215-3219; h) W.-L. Xu, H. Zhang, Y.-L. Hu, H. Yang,
[3] a) E. J. Corey, A. Guzman-Perez, Angew. Chem. Int.
Ed. 1998, 37, 388-401; b) E. J. Corey, Angew. Chem.
Int. Ed. 2002, 41, 1650-1667; c) A. B. Northrup, D. W.
C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458-
2460; d) P. Wessig, G. Müller, Chem. Rev. 2008, 108,
2051-2063; e) J.-L. Li, T.-Y. Liu, Y.-C. Chen, Acc.
Chem. Res. 2012, 45, 1491-1500; f) X. Jiang, R. Wang,
Chem. Rev. 2013, 113, 5515-5546; g) Z. Liu, X. Lin, N.
Yang, Z. Su, C. Hu, P. Xiao, Y. He, Z. Song, J. Am.
Chem. Soc. 2016, 138, 1877-1883; h) M. G. Medvedev,
5
This article is protected by copyright. All rights reserved.