Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Synthesis of C3-Quaternary 2H-Pyrrolines by [3+2] Cycloaddition of Isocyanoacetates and 1,1-Disubstituted Alkenes

Author(s): Yi Cheng, Runmei Zhang, Tianhao Lu, Yong Shen, Min Wang and Chunsong Xie*

Volume 17, Issue 8, 2020

Page: [586 - 589] Pages: 4

DOI: 10.2174/1570178617666191218104959

Price: $65

Abstract

Under mild conditions, C3-quaternary 2H-pyrrolines can be convergently and efficiently assembled by Cu(II) and weak bases cocatalyzed [3+2] cycloaddition of 1,1-disubstituted alkenes and isocyanoacetates. Various functionalities can be tolerated, affording 2H-pyrrolines with up to two quaternary centers in a single step.

Keywords: 2H-pyrroline, copper catalysis, isocyanoacetate, isonitrile, cycloaddition, quaternary carbon.

Graphical Abstract

[1]
Gulevich, A.V.; Zhdanko, A.G.; Orru, R.V.A.; Nenajdenko, V.G. Chem. Rev., 2010, 110(9), 5235-5331.
[http://dx.doi.org/10.1021/cr900411f] [PMID: 20608735]
[2]
a) Hayashi, M.; Iwanaga, M.; Shiomi, N.; Nakane, D.; Masuda, H.; Nakamura, S. Angew. Chem. Int. Ed., 2014, 53, 8411-8415.
[http://dx.doi.org/10.1002/anie.201404629]
b) De la Campa, R.; Ortín, I.; Dixon, D.J. Angew. Chem. Int. Ed., 2015, 54, 4895-4898.
[http://dx.doi.org/10.1002/anie.201411852]
c) Liao, J.Y.; Shao, P.L.; Zhao, Y. J. Am. Chem. Soc., 2015, 137(2), 628-631.
[http://dx.doi.org/10.1021/ja511895q] [PMID: 25555127]
d) Guo, C.; Xue, M-X.; Zhu, M-K.; Gong, L-Z. Angew. Chem. Int. Ed., 2008, 47, 3414-3417.
[http://dx.doi.org/10.1002/anie.200800003]
[3]
Du, J.; Xu, X.; Li, Y.; Pan, L.; Liu, Q. Org. Lett., 2014, 16(15), 4004-4007.
[http://dx.doi.org/10.1021/ol501829k] [PMID: 25055120]
[4]
Xu, X.X.; Zhang, L.J.; Liu, X.Q.; Pan, L.; Liu, Q. Angew. Chem. Int. Ed., 2013, 52, 9271-9274.
[http://dx.doi.org/10.1002/anie.201303604]
[5]
Marti, C.; Carreira, E.M. J. Am. Chem. Soc., 2005, 127(32), 11505-11515.
[http://dx.doi.org/10.1021/ja0518880] [PMID: 16089481]
[6]
a) Magedov, I.V.; Luchetti, G.; Evdokimov, N.M.; Manpadi, M.; Steelant, W.F.A.; Van Slambrouck, S.; Tongwa, P.; Antipin, M.Y.; Kornienko, A. Bioorg. Med. Chem. Lett., 2008, 18(4), 1392-1396.
[http://dx.doi.org/10.1016/j.bmcl.2008.01.019] [PMID: 18221874]
b) Smith, A.B., III; Charnley, A.K.; Hirschmann, R. Acc. Chem. Res., 2011,, 44(3), 180-193.
[http://dx.doi.org/10.1021/ar1001186] [PMID: 21175156]
[7]
a) Sardina, F.J.; Rapoport, H. Chem. Rev., 1996, 96(6), 1825-1872.
[http://dx.doi.org/10.1021/cr9300348] [PMID: 11848813]
b) Coldham, I.; Hufton, R. Chem. Rev., 2005, 105(7), 2765-2810.
[http://dx.doi.org/10.1021/cr040004c] [PMID: 16011324]
c) Pandey, G.; Banerjee, P.; Gadre, S.R. Chem. Rev., 2006, 106(11), 4484-4517.
[http://dx.doi.org/10.1021/cr050011g] [PMID: 17091927]
[8]
a) Shvekhgeimer, M-G.A. Chem. Heterocycl. Compd., 2003.39, 405-448.
[http://dx.doi.org/10.1023/A:1024753027533]
b) Medran, N.S.; La-Venia, A.; Testero, S.A. RSC Advances, 2019, 9, 6804-6844.
[http://dx.doi.org/10.1039/C8RA10247C]
[9]
a) Wang, Z-P.; Xiang, S.; Shao, P.L.; He, Y. J. Org. Chem., 2018.83(18), 10995-11007.
[http://dx.doi.org/10.1021/acs.joc.8]
b) 01622 PMID: 29991251 bWang, Z-P.; Li, Z-R.; Wu, Q.; Peng, X-J.; Shao, P-L.; He, Y. J. Org. Chem., 2017.82(23), 12869-12876.
[http://dx.doi.org/10.1021/acs.joc.7b02266] [PMID: 29087191]
[10]
Morris, B.D.; Prinsep, M.R. Amathaspiramides A-F, novel brominated alkaloids from the marine bryozoan amathia wilsoni. J. Nat. Prod., 1999, 62(5), 688-693.
[http://dx.doi.org/10.1021/np980410p] [PMID: 10346946]
[11]
a) Marradi, M.; Cicchi, S.; Ignacio Delso, J.; Rosi, L.; Tejero, T.; Merino, P.; Goti, A. Tetrahedron Lett., 2005.46, 1287-1290.
[http://dx.doi.org/10.1016/j.tetlet.2004.12.119]
b) Field, L.D.; Messerle, B.A.; Vuong, K.Q.; Turner, P.; Failes, T. Organomet., 2007, 26, 2058-2069.
[http://dx.doi.org/10.1021/om070057v]
[12]
a) Huang, L.; Cheng, H.G.; Zhang, R.M.; Wang, M.; Xie, C.S. Adv. Syn. Cat., 2014.356, 2477-2484.
[http://dx.doi.org/10.1002/adsc.201400376]
b) Cheng, H.G.; Zhang, R.M.; Yang, S.W.; Wang, M.; Zeng, X.F.; Xie, L.J.; Xie, C.S.; Wu, J.; Zhong, G.F. Adv. Synth. Catal., 2016.358, 970-976.
[http://dx.doi.org/10.1002/adsc.201500538]
c) Cheng, H.G.; Zhang, R.M.; Wang, M.; Zeng, X.F.; Xie, C.S. Asian J. Org. Chem., 2018, 7, 1075-1079.
[http://dx.doi.org/10.1002/ajoc.201800222]
[13]
The relative stereochemistry was assigned by a similar method reported in Crich, D.; Banerjee, A. Acc. Chem. Res., 2007. 40, 151- 161. As a result of the shielding effect of the phenyl, the C-2 ester group appeared in a more upfield domain in the endo configuration when compared to the exo configuration.
[14]
In this reaction, Cu(I) and Cu(II) showed similar catalytic activity minght be due to that Cu(II) would disproportionate into Cu(I) in the reaction. Cu(I) might be the catalyticall active species in the reaction. 2002.
[15]
Littke, A.F.; Fu, G.C. Angew. Chem. Int. Ed., 2002, 41, 4176-4211.
[http://dx.doi.org/10.1002/1521-3773(20021115)41:22<4176::AIDANIE4176> 3.0.CO;2-U]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy