Organic Letters
Letter
Jacobs, G.; Mathur, A.; Meng, W.; Ogletree, M. L.; Pi, Z.; Sutton, J. C.;
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Subsequent C−O bond-forming reductive elimination of 5
affords the cycloaddition product 6, which readily decomposes
into intermediate ketene 7 where electron-deficient groups on
the N-phenyl ring stabilize the negatively charged nitrogen atom
and prevent decomposition to imine byproduct.34 An intra-
molecular cyclization of ketene 7 produces enolate 8,35 which is
readily protonated to release the desired β-lactam.
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In conclusion, we developed a modified Kinugasa reaction for
the straightforward preparation of exclusively 4-substituted β-
lactams using calcium carbide as the acetylene source. The
process is convenient and operates under mild conditions using
commercial starting materials that provide a broad reaction
scope. The unsubstituted 3-position opens prospects for lactam
bioconjugation and asymmetric functionalization.
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7817.
(16) Rodygin, K. S.; Werner, G.; Kucherov, F. A.; Ananikov, V. P.
Chem. - Asian J. 2016, 11, 965.
(17) (a) Zhang, W.; Wu, H.; Liu, Z.; Zhong, P.; Zhang, L.; Huang, X.;
Cheng, J. Chem. Commun. 2006, 4826. (b) Hosseini, A.; Pilevar, A.;
Hogan, E.; Mogwitz, B.; Schulze, A. S.; Schreiner, P. R. Org. Biomol.
Chem. 2017, 15, 6800.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures, characterization data, and
spectra for all compounds (PDF)
(18) (a) Sum, Y. N.; Yu, D.; Zhang, Y. Green Chem. 2013, 15, 2718.
(b) Hosseini, A.; Seidel, D.; Miska, A.; Schreiner, P. R. Org. Lett. 2015,
17, 2808.
(19) (a) Werner, G.; Rodygin, K. S.; Kostin, A. A.; Gordeev, E. G.;
Kashin, A. S.; Ananikov, V. P. Green Chem. 2017, 19, 3032.
(b) Rattanangkool, E.; Vilaivan, T.; Sukwattanasinitt, M.;
Wacharasindhu, S. Eur. J. Org. Chem. 2016, 2016, 4347. (c) Matake,
R.; Adachi, Y.; Matsubara, H. Green Chem. 2016, 18, 2614. (d) Teong,
S. P.; Chua, A. Y. H.; Deng, S.; Li, X.; Zhang, Y. Green Chem. 2017, 19,
1659.
AUTHOR INFORMATION
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Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
(20) Yu, D.; Sum, Y. N.; Ean, A. C. C.; Chin, M. P.; Zhang, Y. Angew.
Chem., Int. Ed. 2013, 52, 5125.
(21) Fu, R.; Li, Z. Org. Lett. 2018, 20, 2342.
ACKNOWLEDGMENTS
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(22) (a) Yu, Y.; Huang, W.; Chen, Y.; Gao, B.; Wu, W.; Jiang, H. Green
Chem. 2016, 18, 6445. (b) Yu, Y.; Chen, Y.; Huang, W.; Wu, W.; Jiang,
H. J. Org. Chem. 2017, 82, 9479.
This work was supported by the Justus Liebig University. We
thank Prof. Grzegorz Mloston (U. Lodz) for helpful discussions.
(23) Ledovskaya, M. S.; Rodygin, K. S.; Ananikov, V. P. Org. Chem.
Front. 2018, 5, 226.
(24) (a) Citek, C.; Lyons, C. T.; Wasinger, E. C.; Stack, T. D. P. Nat.
Chem. 2012, 4, 317. (b) Chiang, L.; Keown, W.; Citek, C.; Wasinger, E.
C.; Stack, T. D. P. Angew. Chem. 2016, 128, 10609.
(25) Weissman, S. A.; Anderson, N. G. Org. Process Res. Dev. 2015, 19,
1605.
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