Organic Letters
Letter
Glorius, F. Nature 2014, 510, 485. (k) Menon, R. S.; Biju, A. T.; Nair, V.
Chem. Soc. Rev. 2015, 44, 5040. (l) Flanigan, D. M.; Romanov-
Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307.
(m) Wang, M. H.; Scheidt, K. A. Angew. Chem., Int. Ed. 2016, 55, 14912.
(n) Wang, Z.; Pan, D.; Li, T.; Jin, Z. Chem. - Asian J. 2018, 13, 2149.
(o) Mondal, S.; Yetra, S. R.; Mukherjee, S.; Biju, A. T. Acc. Chem. Res.
2019, 52, 425. (p) De Risi, C.; Bortolini, O.; Di Carmine, G.; Ragno, D.;
Massi, A. Synthesis 2019, 51, 1871.
ACKNOWLEDGMENTS
■
We thank Dr. Yongxin Li (NTU) and Dr. Rakesh Ganguly for
assistance with X-ray structure analysis. We acknowledge
financial support from the National Natural Science Foundation
of China (21772029, 21801051 and 21961006); National Key
Technologies R&D Program (2014BAD23B01); The 10 Talent
Plan (Shicengci) of Guizhou Province ([2016]5649); the
Guizhou Province Returned Oversea Student Science and
Technology Activity Program [(2014)-2], the Science and
Technology Department of Guizhou Province ([2018]2802,
[2019]1020); the Program of Introducing Talents of Discipline
to Universities of China (111 Program, D20023) Guizhou
University; the Guizhou Province First-Class Disciplines Project
[(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], Guizhou
University of Traditional Chinese Medicine (China); Singapore
National Research Foundation (NRF-NRFI2016-06), the
Ministry of Education of Singapore (MOE2013-T2-2-003,
MOE2016-T2-1-032, RG108/16, RG5/19, RG1/18,
MOE2018-T3-1-003); A*STAR Individual Research Grant
(A1783c0008); and Nanyang Research Award Grant, and
Nanyang Technological University.
(9) For selected examples on kinetic resolution via NHC catalyzed
reaction, see: (a) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M.
Chem. Commun. 2004, 2770. (b) Kano, T.; Sasaki, K.; Maruoka, K. Org.
Lett. 2005, 7, 1347. (c) Li, G.-Q.; Li, Y.; Dai, L.-X.; You, S.-L. Adv. Synth.
Catal. 2008, 350, 1258. (d) De Sarkar, S.; Biswas, A.; Song, C.; Studer,
A. Synthesis 2011, 2011, 1974. (e) Binanzer, M.; Hsieh, S.-Y.; Bode, J.
W. J. Am. Chem. Soc. 2011, 133, 19698. (f) Kuwano, S.; Harada, S.;
Kang, B.; Oriez, R.; Yamaoka, Y.; Takasu, K.; Yamada, K. J. Am. Chem.
Soc. 2013, 135, 11485. (g) Lu, S.; Poh, S. B.; Siau, W.-Y.; Zhao, Y.
Angew. Chem., Int. Ed. 2013, 52, 1731. (h) Lu, S.; Poh, S. B.; Zhao, Y.
Angew. Chem., Int. Ed. 2014, 53, 11041. (i) Wang, M.; Huang, Z.; Xu, J.;
Chi, Y. R. J. Am. Chem. Soc. 2014, 136, 1214. (j) Allen, S. E.; Hsieh, S.-
Y.; Gutierrez, O.; Bode, J. W.; Kozlowski, M. C. J. Am. Chem. Soc. 2014,
136, 11783. (k) Dong, S.; Frings, M.; Cheng, H.; Wen, J.; Zhang, D.;
Raabe, G.; Bolm, C. J. Am. Chem. Soc. 2016, 138, 2166. (l) Liu, B.; Yan,
J.; Huang, R.; Wang, W.; Jin, Z.; Zanoni, G.; Zheng, P.; Yang, S.; Chi, Y.
R. Org. Lett. 2018, 20, 3447. (m) Bie, J.; Lang, M.; Wang, J. Org. Lett.
2018, 20, 5866. (n) Chen, X.-Y.; Li, S.; Liu, Q.; Kumar, M.; Peuronen,
A.; Rissanen, K.; Enders, D. Chem. - Eur. J. 2018, 24, 9735.
(o) Bhattacharya, A.; Shukla, P.; Kaushik, L. K.; Maji, B. Org. Chem.
Front. 2019, 6, 3523. For selected examples on dynamic kinetic
resolution via NHC-catalyzed reaction, see: (p) Cohen, D. T.;
Eichman, C. C.; Phillips, E. M.; Zarefsky, E. R.; Scheidt, K. A. Angew.
Chem., Int. Ed. 2012, 51, 7309. (q) Johnston, R. C.; Cohen, D. T.;
Eichman, C. C.; Scheidt, K. A.; Cheong, P. H.-Y. Chem. Sci. 2014, 5,
1974. (r) Goodman, C. G.; Johnson, J. S. J. Am. Chem. Soc. 2014, 136,
14698. (s) Goodman, C. G.; Walker, M. M.; Johnson, J. S. J. Am. Chem.
Soc. 2015, 137, 122. (t) Wu, Z.; Li, F.; Wang, J. Angew. Chem., Int. Ed.
2015, 54, 1629. (u) Zhao, C.; Li, F.; Wang, J. Angew. Chem., Int. Ed.
2016, 55, 1820. (v) Zhang, G.; Yang, S.; Zhang, X.; Lin, Q.; Das, D. K.;
Liu, J.; Fang, X. J. Am. Chem. Soc. 2016, 138, 7932. (w) Mondal, S.;
Mukherjee, S.; Das, T. K.; Gonnade, R.; Biju, A. T. ACS Catal. 2017, 7,
3995. (x) Chen, K.-Q.; Gao, Z.-H.; Ye, S. Angew. Chem., Int. Ed. 2019,
58, 1183.
REFERENCES
■
(1) (a) Tal, A.; Zarka, S.; Rubin, B. Pestic. Biochem. Physiol. 1996, 56,
134. (b) Friesen, L. F.; Jones, T. L.; Van Acker, R. C.; Morrison, I. N.
Weed Sci. 2000, 48, 532. (c) Kolmodin-Hedman, B.; Hoglund, S.;
̈
Åkerblom, M. Arch. Toxicol. 1983, 54, 257. (d) Shrestha, S.; Bhattarai,
B. R.; Cho, H.; Choi, J.-K.; Cho, H. Bioorg. Med. Chem. Lett. 2007, 17,
2728. (e) Feller, D. R.; Kamanna, V. S.; Newman, H. A. I.; Romstedt, K.
J.; Witiak, D. T.; Bettoni, G.; Bryant, S. H.; Camerino, D. C.; Loiodice,
F.; Tortorella, V. J. Med. Chem. 1987, 30 (8), 1265. (f) Zhang, Z.-Y.;
Lee, S.-Y. Expert Opin. Invest. Drugs 2003, 12, 223.
(2) (a) Carocci, A.; Catalano, A.; Lovece, A.; Lentini, G.; Duranti, A.;
Lucini, V.; Pannacci, M.; Scaglione, F.; Franchini, C. Bioorg. Med. Chem.
2010, 18, 6496. (b) Williams, J. D.; Torhan, M. C.; Neelagiri, V. R.;
Brown, C.; Bowlin, N. O.; Di, M.; McCarthy, C. T.; Aiello, D.; Peet, N.
P.; Bowlin, T. L.; Moir, D. T. Bioorg. Med. Chem. 2015, 23, 1027.
(3) (a) Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010,
49, 2175. (b) Fujita, M.; Yoshida, Y.; Miyata, K.; Wakisaka, A.;
Sugimura, T. Angew. Chem., Int. Ed. 2010, 49, 7068. (c) Fujita, M.;
Wakita, M.; Sugimura, T. Chem. Commun. 2011, 47, 3983.
(4) (a) Maligres, P. E.; Krska, S. W.; Humphrey, G. R. Org. Lett. 2004,
6, 3147. (b) Chen, C.; Zhu, S.-F.; Liu, B.; Wang, L.-X.; Zhou, Q.-L. J.
Am. Chem. Soc. 2007, 129, 12616. (c) Li, S.; Zhu, S.-F.; Xie, J.-H.; Song,
S.; Zhang, C.-M.; Zhou, Q.-L. J. Am. Chem. Soc. 2010, 132, 1172.
(d) Song, S.; Zhu, S.-F.; Li, Y.; Zhou, Q.-L. Org. Lett. 2013, 15, 3722.
(e) Xie, X.-L.; Zhu, S.-F.; Guo, J.-X.; Cai, Y.; Zhou, Q.-L. Angew. Chem.,
Int. Ed. 2014, 53, 2978. (f) Yao, L.; Wen, J.; Liu, S.; Tan, R.; Wood, N.
M.; Chen, W.; Zhang, S.; Zhang, X. Chem. Commun. 2016, 52, 2273.
(5) (a) Um, P.-J.; Drueckhammer, D. G. J. Am. Chem. Soc. 1998, 120,
5605. (b) Kato, D.; Mitsuda, S.; Ohta, H. Org. Lett. 2002, 4, 371.
(c) Kato, D.; Mitsuda, S.; Ohta, H. J. Org. Chem. 2003, 68, 7234.
(6) Yang, X.; Birman, V. B. Chem. - Eur. J. 2011, 17, 11296.
(10) Engers, J. L.; Bollinger, K. A.; Weiner, R. L.; Rodriguez, A. L.;
Long, M. F.; Breiner, M. M.; Chang, S.; Bollinger, S. R.; Bubser, M.;
Jones, C. K.; Morrison, R. D.; Bridges, T. M.; Blobaum, A. L.;
Niswender, C. M.; Conn, P. J.; Emmitte, K. A.; Lindsley, C. W. ACS
Med. Chem. Lett. 2017, 8, 925.
(11) (a) Hao, L.; Du, Y.; Lv, H.; Chen, X.; Jiang, H.; Shao, Y.; Chi, Y.
R. Org. Lett. 2012, 14, 2154. (b) Hao, L.; Chen, S.; Xu, J.; Tiwari, B.; Fu,
Z.; Li, T.; Lim, J.; Chi, Y. R. Org. Lett. 2013, 15, 4956.
(12) (a) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc.
2002, 124, 10298. (b) He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem.
Soc. 2006, 128, 8418. (c) Raup, D. E. A.; Cardinal-David, B.; Holte, D.;
Scheidt, K. A. Nat. Chem. 2010, 2, 766. (d) Chiang, P.-C.; Rommel, M.;
Bode, J. W. J. Am. Chem. Soc. 2009, 131, 8714.
(7) Chen, X.; Fong, J. Z. M.; Xu, J.; Mou, C.; Lu, Y.; Yang, S.; Song, B.-
A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7212.
(8) For selected reviews on NHC catalysis, see: (a) Enders, D.;
Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606. (b) Marion, N.;
́
Díez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
(c) Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182.
(d) Douglas, J.; Churchill, G.; Smith, A. D. Synthesis 2012, 44, 2295.
(e) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511. (f) Vora, H.
U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617.
(g) Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew.
Chem., Int. Ed. 2012, 51, 11686. (h) Cohen, D. T.; Scheidt, K. A. Chem.
Sci. 2012, 3, 53. (i) Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc.
Rev. 2013, 42, 4906. (j) Hopkinson, M. N.; Richter, C.; Schedler, M.;
D
Org. Lett. XXXX, XXX, XXX−XXX