Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Modular Synthesis of New Bicyclic Carbene Precursors

Author(s): Jie Li, Jiaqi Yao, Weiping He, Fan Yang and Xiaoming Liu*

Volume 16, Issue 12, 2019

Page: [951 - 954] Pages: 4

DOI: 10.2174/1570178616666190212125426

Price: $65

Abstract

A series of new N-heterocyclic carbene (NHC) precursors, containing bicyclic pyrrolo[1,2- c]imidazole framework, were prepared from N-(tert-butoxycarbonyl)-L-proline (1-Boc-L-proline). The sequential attachment of nitrogen nucleophiles and subsequent ring closure gave the desired bicyclic NHC precursors in good yields. The structures of these new NHC precursors were determined on the basis of spectroscopic techniques, including NMR and MS.

Keywords: N-heterocyclic carbene, proline, synthesis, chirality, nitrogen nucleophiles, precursors.

« Previous Next »
Graphical Abstract

[1]
Öfele, K. J. Organomet. Chem., 1968, 12, 42-43.
[2]
Wanzlick, H.W.; Schönherr, H.J. Angew. Chem. Int. Ed. Engl., 1968, 7, 141-142.
[3]
Arduengo, A.J., III; Harlow, R.L.; Kline, M. J. Am. Chem. Soc., 1991, 113, 361-363.
[4]
Herrmann, W.A.; Köcher, C. Angew. Chem. Int. Ed. , 1997, 36, 2162-2187.
[5]
Bourissou, D.; Guerret, O.; Gabbaï, F.P.; Bertrand, G. Chem. Rev., 2000, 100, 39-92.
[6]
Zinn, F.K.; Viciu, M.S.; Nolan, S.P. Annu. Rep. Prog. Chem. Sect. B: Org. Chem., 2004, 100, 231-249.
[7]
Cavell, K.J.; McGuinness, D.S. Coord. Chem. Rev., 2004, 248, 671-681.
[8]
Peris, E.; Crabtree, R.H. Coord. Chem. Rev., 2004, 248, 2239-2246.
[9]
Crudden, C.M.; Allen, D.P. Coord. Chem. Rev., 2004, 248, 2247-2273.
[10]
Pugh, D.; Danopoulos, A.A. Coord. Chem. Rev., 2007, 251, 610-641.
[11]
Mata, J.A.; Poyatos, M.; Peris, E. Coord. Chem. Rev., 2007, 251, 841-859.
[12]
Sommer, W.J.; Weck, M. Coord. Chem. Rev., 2007, 251, 860-873.
[13]
Hahn, F.E.; Jahnke, M.C. Angew. Chem. Int. Ed., 2008, 47, 3122-3172.
[14]
Hopkinson, M.N.; Richter, C.; Schedler, M.; Glorius, F. Nature, 2014, 510, 485-496.
[15]
Perry, M.C.; Burgess, K. Tetrahedron Asymmetry, 2003, 14, 951-961.
[16]
César, V.; Bellemin-Laponnaz, S.; Gade, L.H. Chem. Soc. Rev., 2004, 33, 619-636.
[17]
Douthwaite, R.E. Chem. Rev., 2007, 251, 702-717.
[18]
Gade, L.H.; Bellemin-Laponnaz, S. Chem. Rev., 2007, 251, 718-725.
[19]
Snead, D.R.; Seo, H.; Hong, S. Curr. Org. Chem., 2008, 12, 1370-1387.
[20]
Wang, F.; Liu, L.j.; Wang, W.; Li, S.; Shi, M. Coord. Chem. Rev., 2012, 256, 804-853.
[21]
Grossmann, A.; Enders, D. Angew. Chem. Int. Ed., 2012, 51, 314-325.
[22]
Bugaut, X.; Glorius, F. Chem. Soc. Rev., 2012, 41, 3511-3522.
[23]
Flanigan, D.M.; Romanov-Michailidis, F.; White, N.A.; Rovis, T. Chem. Rev., 2015, 115, 9307-9387.
[24]
Wang, A.; Xiao, Y.; Zhou, Y.; Xu, J.; Liu, H. Youji Huaxue (Chin. J. Org. Chem.), 2017, 37, 2590-2608.
[25]
Van Veldhuizen, J.J.; Garber, S.B.; Kingsbury, J.S.; Hoveyda, A.H. J. Am. Chem. Soc., 2002, 124, 4954-4955.
[26]
Mehnert, C.P.; Cook, R.A.; Dispenziere, N.C.; Afeworki, M. J. Am. Chem. Soc., 2002, 124, 12932-12933.
[27]
Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M.B. Angew. Chem. Int. Ed., 2003, 42, 5871-5874.
[28]
Alcarazo, M.; Roseblade, S.J.; Alonso, E.; Fernandez, R.; Alvarez, E.; Lahoz, F.J.; Lassaletta, J.M. J. Am. Chem. Soc., 2004, 126, 13242-13243.
[29]
Paczal, A.; Bényei, A.C.; Kotschy, A. J. Org. Chem., 2006, 71, 5969-5979.
[30]
César, V.; Lugan, N.; Lavigne, G. J. Am. Chem. Soc., 2008, 130, 11286-11287.
[31]
Hudnall, T.W.; Bielawski, C.W. J. Am. Chem. Soc., 2009, 131, 16039-16041.
[32]
Park, J.K.; Lackey, H.H.; Rexford, M.D.; Kovnir, K.; Shatruk, M.; McQuade, D.T. Org. Lett., 2010, 12, 5008-5011.
[33]
Li, J.; Xu, L. Tetrahedron, 2015, 71, 2858-2862.
[34]
He, W.P.; Zhou, B.H.; Zhou, Y.L.; Li, X.R.; Fan, L.M.; Shou, H.W.; Li, J. Tetrahedron Lett., 2016, 57, 3152-3155.
[35]
Zhou, B-H.; He, W-P.; Li, L-L.; Fan, L-M.; Li, X-R.; Li, J. Curr. Org. Synth., 2018, 15, 137-142.
[36]
Kwak, J.H.; Kim, Y.; Park, H.; Jang, J-Y.; Lee, K.K.; Yi, W.; Kwak, J.A.; Park, S.G.; Kim, H.; Lee, K.; Kang, J.S.; Han, S-B.; Hwang, B.Y.; Hong, J.T.; Jung, J.K.; Kim, Y.; Cho, J.; Lee, H. Bioorg. Med. Chem. Lett., 2010, 20, 4620-4623.
[37]
Yadav, G.D.; Singh, S. Tetrahedron Asymmetry, 2016, 27, 123-129.
[38]
Chakraborti, G.; Paladhi, S.; Mandal, T.; Dash, J. J. Org. Chem., 2018, 83, 7347-7359.
[39]
Clayden, J.; Foricher, Y.J.Y.; Helliwell, M.; Johnson, P.; Mitjans, D.; Vinader, V. Org. Biomol. Chem., 2006, 4, 444-454.

Rights & Permissions Print Cite
Article Metrics
41
1
© 2024 Bentham Science Publishers | Privacy Policy