Organic Letters
Letter
Recent Advances in the Catalytic Enantioselective Reactions of para-
Quinone Methides. Chem. - Asian J. 2018, 13, 2350.
ACKNOWLEDGMENTS
■
The project described was supported by Award R35
GM118055 from the National Institute of General Medical
Sciences. M.F.M. is an NSF Graduate Research Fellowship.
T.C. acknowledges support from the North Carolina School of
Science and Mathematics (NCSSM). We thank the UNC
Department of Chemistry Mass Spectrometry Core Labo-
ratory, especially Dr. Brandie Ehrmann, for assistance with
mass spectrometry analysis on instrumentation acquired
through the NSF MRI program under Award CHE-1726291.
We thank the UNC Department of Chemistry NMR Core
Laboratory, especially Dr. Marc ter Horst, for assistance with
NMR analysis on instrumentation acquired through the NSF
MRI program under Award CHE-1828183.
(9) For a recent example of a 1,6-conjugate addition resulting in
rearomatized products, see: Shirsath, S. R.; Shinde, G. H.; Shaikh, A.
C.; Muthukrishnan, M. Accessing α-Arylated Nitriles via BF3·OEt2
Catalyzed Cyanation of para-Quinone Methides Using tert-Butyl
Isocyanide as a Cyanide Source. J. Org. Chem. 2018, 83, 12305.
(10) For examples of 1,6-conjugate addition to stable pQMs
resulting in dearomatized products, see: (a) Yuan, Z.; Fang, X.; Li, X.;
Wu, J.; Yao, H.; Lin, A. 1,6-Conjugated Addition-Mediated [2 + 1]
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2015, 80, 11123. (b) Ma, C.; Huang, Y.; Zhao, Y. Stereoselective 1,6-
Conjugate Addition/Annulation of para-Quinone Methides with
Vinyl Epoxides/Cyclopropanes. ACS Catal. 2016, 6, 6408. (c) Roiser,
L.; Waser, M. Enantioselective Spirocyclopropanation of para-
Quinone Methides Using Ammonium Ylides. Org. Lett. 2017, 19,
2338. (d) Su, Y.; Zhao, Y.; Chang, B.; Zhao, X.; Zhang, R.; Liu, X.;
Huang, D.; Wang, K.; Huo, C.; Hu, Y. [3 + 2] Cycloaddition of para-
Quinone Methides with Nitrile Imines: Approach to Spiro-pyrazoline-
cyclohexadienones. J. Org. Chem. 2019, 84, 6719.
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