Organic Letters
Letter
Y.-R.; Yang, H.; Hu, J. Org. Biomol. Chem. 2016, 14, 3098. (d) Zhang,
X.-Z.; Ge, D.-L.; Chen, S.-Y.; Yu, X.-Q. RSC Adv. 2016, 6, 66320.
(9) For selected reviews on alkene difunctionalization by other
methods, see: (a) Yin, G.; Mu, X.; Liu, G. Acc. Chem. Res. 2016, 49,
AUTHOR INFORMATION
■
Corresponding Author
ORCID
2413. (b) Muniz, K. Acc. Chem. Res. 2018, 51, 1507.
̃
(10) (a) Denmark, S. E.; Collins, W. R. Org. Lett. 2007, 9, 3801.
(b) Denmark, S. E.; Kornfilt, D. J. P.; Vogler, T. J. Am. Chem. Soc.
2011, 133, 15308. (c) Denmark, S. E.; Jaunet, A. J. Am. Chem. Soc.
2013, 135, 6419. (d) Denmark, S. E.; Chi, H. M. J. Am. Chem. Soc.
2014, 136, 8915. (e) Denmark, S. E.; Chi, H. M. J. Am. Chem. Soc.
2014, 136, 3655. (f) Denmark, S. E.; Rossi, S.; Webster, M. P.; Wang,
H. J. Am. Chem. Soc. 2014, 136, 13016. (g) Denmark, S. E.;
Hartmann, E.; Kornfilt, D. J. P.; Wang, H. Nat. Chem. 2014, 6, 1056.
(h) Denmark, S. E.; Chi, H. M. J. Org. Chem. 2017, 82, 3826. (i) Tao,
Z.; Robb, K. A.; Zhao, K.; Denmark, S. E. J. Am. Chem. Soc. 2018, 140,
3569.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank the National Natural Science Foundation of China
(Grant Nos. 21772239 and 91856109) and the Natural
Science Foundation of Guangdong Province (Grant No.
2014A030312018) for financial support.
(11) (a) Balkrishna, S. J.; Prasad, C. D.; Panini, P.; Detty, M. R.;
Chopra, D.; Kumar, S. J. Org. Chem. 2012, 77, 9541. (b) Tay, D. W.;
Tsoi, I. T.; Er, J. C.; Leung, G. Y. C.; Yeung, Y.-Y. Org. Lett. 2013, 15,
1310. (c) Chen, F.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2013,
135, 1232. (d) See, J. Y.; Yang, H.; Zhao, Y.; Wong, M. W.; Ke, Z.;
Yeung, Y.-Y. ACS Catal. 2018, 8, 850.
(12) (a) Luo, J.; Zhu, Z.; Liu, Y.; Zhao, X. Org. Lett. 2015, 17, 3620.
(b) Luo, J.; Liu, X.; Zhao, X. Synlett 2017, 28, 397. (c) Zhu, Z.; Luo,
J.; Zhao, X. Org. Lett. 2017, 19, 4940. (d) Luo, J.; Liu, Y.; Zhao, X.
Org. Lett. 2017, 19, 3434. (e) Liu, X.; Liang, Y.; Ji, J.; Luo, J.; Zhao, X.
J. Am. Chem. Soc. 2018, 140, 4782. (f) Luo, J.; Cao, Q.; Cao, X.; Zhao,
X. Nat. Commun. 2018, 9, 527. (g) Xu, J.; Zhang, Y.; Qin, T.; Zhao, X.
Org. Lett. 2018, 20, 6384.
(13) (a) Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53,
9316. (b) Wu, D.; Qiu, J.; Karmaker, P. G.; Yin, H.; Chen, F.-X. J.
Org. Chem. 2018, 83, 1576.
(14) (a) Pasquato, L.; Modena, G. Chem. Commun. 1999, 1469.
(b) Denmark, S. E.; Vogler, T. Chem. - Eur. J. 2009, 15, 11737.
(15) (a) Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani,
D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207. (b) Hansch, C.; Leo, A.;
Taft, R. W. Chem. Rev. 1991, 91, 165. (c) Leroux, F.; Jeschke, P.;
REFERENCES
■
(1) For reviews, see: (a) Witczak, Z. J. Adv. Carbohydr. Chem.
Biochem. 1987, 44, 91. (b) Erian, A. W.; Sherif, S. M. Tetrahedron
1999, 55, 7957. (c) Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea,
M. Chem. Soc. Rev. 2016, 45, 494. (d) Xu, Q.; Zhang, L.; Feng, G.; Jin,
C. Youji Huaxue 2019, 39, 287.
(2) (a) Johnson, T. B.; Douglass, I. B. J. Am. Chem. Soc. 1939, 61,
2548. (b) Riemschneider, R.; Wojahn, F.; Orlick, G. J. Am. Chem. Soc.
1951, 73, 5905. (c) Grieco, P. A.; Yokoyama, Y.; Williams, E. J. Org.
Chem. 1978, 43, 1283. (d) Bunyagidj, C.; Piotrowska, H.; Aldridge,
M. H. J. Org. Chem. 1981, 46, 3335. (e) Wei, Z.-L.; Kozikowski, A. P.
J. Org. Chem. 2003, 68, 9116. (f) Bayarmagnai, B.; Matheis, C.;
Jouvin, K.; Goossen, L. J. Angew. Chem., Int. Ed. 2015, 54, 5753.
(g) Chen, J.; Wang, T.; Wang, T.; Lin, A.; Yao, H.; Xu, J. Org. Chem.
Front. 2017, 4, 130. (h) See, J. Y.; Zhao, Y. Org. Lett. 2018, 20, 7433.
(i) Yuan, P.-F.; Zhang, Q.-B.; Jin, X.-L.; Lei, W.-L.; Wu, L.-Z.; Liu, Q.
Green Chem. 2018, 20, 5464.
(3) (a) He, H.-y.; Faulkner, D. J. J. Org. Chem. 1989, 54, 2511.
(b) Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.;
Faucette, L.; Johnson, R. K.; Faulkner, D.J. Tetrahedron Lett. 1997, 38,
363. (c) Szajnman, S. H.; Yan, W.; Bailey, B. N.; Docampo, R.;
Schlosser, M. Chem. Rev. 2005, 105, 827. (d) Muller, K.; Faeh, C.;
̈
Diederich, F. Science 2007, 317, 1881. (e) Manteau, B.; Pazenok, S.;
Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140.
Elhalem, E.; Rodriguez, J. B. J. Med. Chem. 2000, 43, 1826. (d) Pina, I.
̃
C.; Gautschi, J. T.; Wang, G.-Y.-S.; Sanders, M. L.; Schmitz, F. J.;
France, D.; Cornell-Kennon, S.; Sambucetti, L. C.; Remiszewski, S.
W.; Perez, L. B.; Bair, K. W.; Crews, P. J. Org. Chem. 2003, 68, 3866.
(e) Yasman; Edrada, R. A.; Wray, V.; Proksch, P. J. Nat. Prod. 2003,
66, 1512. (f) Singh, P.; Bhardwaj, A. J. Med. Chem. 2010, 53, 3707.
(g) Fortes, M. P.; da Silva, P. B. N.; da Silva, T. G.; Kaufman, T. S.;
̃
Militao, G. C. G.; Silveira, C. C. Eur. J. Med. Chem. 2016, 118, 21.
(h) Alcolea, V.; Plano, D.; Encío, I.; Palop, J. A.; Sharma, A. K.;
Sanmartín, C. Eur. J. Med. Chem. 2016, 123, 407.
(4) (a) Zhu, N.; Wang, F.; Chen, P.; Ye, J.; Liu, G. Org. Lett. 2015,
17, 3580. (b) Liang, Z.; Wang, F.; Chen, P.; Liu, G. Org. Lett. 2015,
17, 2438. (c) Tao, Z.-K.; Li, C.-K.; Zhang, P.-Z.; Shoberu, A.; Zou, J.-
P.; Zhang, W. J. Org. Chem. 2018, 83, 2418. (d) Wang, L.-J.; Ren, P.-
X.; Lin, Q.; Chen, M.; Lu, Y.-L.; Zhao, J.-Y.; Liu, R.; Chen, J.-M.; Li,
W. Org. Lett. 2018, 20, 4411.
(5) (a) Zhang, D.; Wang, H.; Bolm, C. Chem. Commun. 2018, 54,
5772. (b) Gullapalli, K.; Vijaykumar, S. Org. Biomol. Chem. 2019, 17,
2232. (c) Hoque, I. U.; Chowdhury, S. R.; Maity, S. J. Org. Chem.
2019, 84, 3025. (d) Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019,
84, 2243.
(6) Feng, Y.; Hussain, M. I.; Zhang, X.; Shi, J.; Hu, W.; Xiong, Y.
Tetrahedron 2018, 74, 2669.
(7) (a) Ye, A.-H.; Zhang, Y.; Xie, Y.-Y.; Luo, H.-Y.; Dong, J.-W.; Liu,
X.-D.; Song, X.-F.; Ding, T.; Chen, Z.-M. Org. Lett. 2019, 21, 5106.
(b) Li, C.; Long, P.; Wu, H.; Yin, H.; Chen, F.-X. Org. Biomol. Chem.
2019, 17, 7131.
(8) (a) Yang, H.; Duan, X.-H.; Zhao, J.-F.; Guo, L.-N. Org. Lett.
2015, 17, 1998. (b) Egami, H.; Yoneda, T.; Uku, M.; Ide, T.; Kawato,
Y.; Hamashima, Y. J. Org. Chem. 2016, 81, 4020. (c) Guo, L.-N.; Gu,
E
Org. Lett. XXXX, XXX, XXX−XXX