Chemistry - A European Journal
10.1002/chem.201602229
COMMUNICATION
Numata, Heterocycles 2004, 63, 1123; e) Y. Feng, J. W. Blunt, A. L. J.
Cole, M. H. G. Munro, J. Nat. Prod. 2004, 67, 2090; f) J.-Y. Dong, H.-P.
He, Y.-M. Shen, K.-Q. Zhang, J. Nat. Prod. 2005, 68, 1510; g) C.-J.
Zheng, C -J. Kim, K. S. Bae, Y.-H. Kim, W.-G. Kim, J. Nat. Prod. 2006,
69, 1816; h) B. V. Bertinetti, M. A. Rodriguez, A. M. Godeas, G. M.
Cabrera, J. Antibiot. 2010, 63, 681.
[6]
For selected examples of using the dearomatization of indoles as a key
step to assemble pyrroloindoline alkaloids, see: (a) M. Zhang, X. Huang,
L. Shen, Y. Qin, J. Am. Chem. Soc. 2009, 131, 6013; b) S. B. Jones, B.
Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606; c)
Z. Zuo, W. Xie, D. Ma, J. Am. Chem. Soc. 2010, 132, 13226; d) R. R.
Knowles, J. Carpenter, S. B. Blakey, A. Kayano, I. K. Mangion, C. J.
Sinz, D. W. C. MacMillan, Chem. Sci. 2011, 2, 308; e) S. B. Jones, B.
Simmons, A. Mastracchio, D. W. C. MacMillan, Nature. 2011, 475, 183;
f) Z. Zuo, D. Ma, Angew. Chem. 2011, 123, 12214; Angew. Chem., Int.
Ed. 2011, 50, 12008; g) W. Zi, W. Xie, D. Ma, J. Am. Chem. Soc. 2012,
134, 9126; h) B. D. Horning, D. W. C. MacMillan, J. Am. Chem. Soc.
2013, 135, 6442; i) B. N. Laforteza, M. Pickworth, D. W. C. MacMillan,
Angew. Chem. 2013, 125, 11479; Angew. Chem., Int. Ed., 2013 52,
11269; j) Y. Wei, D. Zhao, D. Ma, Angew. Chem. 2013, 125, 13226;
Angew. Chem., Int. Ed. 2013, 52, 12988; k) M. Teng, W. Zi, D. Ma,
Angew. Chem. 2014, 126, 1845; Angew. Chem., Int. Ed. 2014, 53,
1814; l) H. Wang, S. E. Reisman, Angew. Chem. 2014, 126, 6320;
Angew. Chem., Int. Ed. 2014, 53, 6206; m) C. Liu, J.-C. Yi, Z.-B. Zheng,
Y. Tang, L.-X. Dai, S.-L. You, Angew. Chem. 2016, 128, 761; Angew.
Chem. Int. Ed. 2016, 55, 751.
[2]
a) L. E. Overman, Y. Shin, Org. Lett. 2007, 9, 339; b) J. E. Delorbe, S.
Y. Jabri, S. M. Mennen, L. E. Overman, F.-L. Zhang, J. Am. Chem. Soc.
2011, 133, 6549; c) L. Furst, J. M. R. Narayanam, C. R. J. Stephenson,
Angew. Chem. 2011, 123, 9829; Angew. Chem., Int. Ed. 2011, 50,
9655; d) B. M. Trost, J. Xie, J. D. Sieber, J. Am. Chem. Soc. 2011, 133,
20611; e) N. Boyer, M. Movassaghi, Chem. Sci. 2012, 3, 1798; f) N.
Boyer, K. C. Morrison, J. Kim, P. J. Hergenrother, M. Movassaghi,
Gong, Chem. Eur. J. 2013, 19, 3319; h) J. E. DeLorbe, D. Horne, R.
Jove, S. M. Mennen, S. Nam, F.-L. Zhang, L. E. Overman, J. Am.
Chem. Soc. 2013, 135, 4117; i) S. Y. Jabri, L. E. Overman, J. Am.
Chem. Soc. 2013, 135, 4231.
[3]
[4]
For recent reviews on dearomatization reaction of indoles, see: a) C.-X.
Zhuo, W. Zhang, S.-L.You, Angew. Chem. 2012, 124, 12834; Angew.
Chem., Int. Ed. 2012, 51, 12662.; b) L. M. Repka, S. E. Reisman, J.
Org. Chem. 2013, 78, 12314; c) Q. Ding, X. Zhou, R. Fan, Org. Biomol.
Chem. 2014, 12, 4807; d) C.-X. Zhuo, C. Zheng, S.-L. You, Acc. Chem.
Res. 2014, 47, 2558.
[7]
a) S. Zhu, D. W. C. MacMillan, J. Am. Chem. Soc. 2012, 134, 10815; b)
M. E. Kieffer, K. V. Chuang, S. E. Reisman, Chem. Sci. 2012, 3, 3170;
c) M. E.; Kieffer, K. V. Chuang, S. E. Reisman, J. Am. Chem. Soc. 2013,
135, 5557; d) C. Liu, W. Zhang, L.-X. Dai, S.-L. You, Org. Lett. 2012, 14,
4525. [Corrections: Org. Lett. 2012, 14, 5168.]
For selected organocatalytic asymmetric dearomatization of indoles,
see: a) J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C.
MacMillan, Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482; b) C. Gioia, A.
Hauville, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. 2008, 120, 9376;
Angew. Chem., Int. Ed. 2008, 47, 9236; c) O. Lozano, G. Blessley, T. M.
del Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R.
Borman, V. Gouverneur, Angew. Chem. 2011, 123, 8255; Angew.
Chem., Int. Ed. 2011, 50, 8105; d) F. Kolundzic, M. N. Noshi, M.
Tjandra, M. Movassaghi, S. J. Miller, J. Am. Chem. Soc. 2011, 133,
9104; e) B. Tan, G. Hernández-Torres, C. F. Barbas, III. J. Am. Chem.
Soc. 2011, 133, 12354; f) Z. Zhang, J. C. Antilla, Angew. Chem. 2012,
124, 11948; Angew. Chem., Int. Ed. 2012, 51, 11778; g) W. Xie, G.
Jiang, H. Liu, J. Hu, X. Pan, H. Zhang, X. Wan, Y. Lai, D. Ma, Angew.
Chem. 2013, 125, 13162; Angew. Chem., Int. Ed. 2013, 52, 12924; h)
H. M. Nelson, S. H. Reisberg, H. P. Shunatona, J. S. Patel, F. D. Toste,
Angew. Chem. 2014, 126, 5706; Angew. Chem., Int. Ed. 2014, 53,
5600; i) L. Liao, C. Shu, M. Zhang, Y. Liao, X. Hu, Y. Zhang, Z. Wu, W.
Yuan, X. Zhang, Angew. Chem. 2014, 126, 10639; Angew. Chem., Int.
Ed. 2014, 53, 10471; j) C. S. Yeung, R. E. Ziegler, Jr, J. A. Porco, E. N.
Jacobsen, J. Am. Chem. Soc. 2014, 136, 13614; k) Y.-C. Zhang, J.-J.
Zhao, F. Jiang, S.-B. Sun, F. Shi, Angew. Chem. 2014, 126, 14132;
Angew. Chem., Int. Ed. 2014, 53, 13912.
[8]
a) B. Y. Karele, L. E. Treigute, S. V. Kalnin, I. P. Grinberga, O. Y.
Neiland, Khim. Geterotsilkl. Soedin., 1974, 2, 214; b) M. S. Ermolenko,
V. A. Budylin, A. N. Kost, Khim. Geterotsikl. Soedin. 1978, 7, 933; c) V.
A. Budylin, M. S. Ermolenko, F. A. Chugtai, P. A. Sharbatyan, A. N.
Kost, Khim. Geterotsikl. Soedin. 1981, 11, 1503; d) J. S. Harvey, S. P.
Simonovich, C. R. Jamison, D. W. C. MacMillan, J. Am. Chem. Soc.
2011, 133, 13782.
[9]
For selected examples: a) Q. Cai, C. Zheng, J.-W. Zhang, S.-L. You,
Angew. Chem. 2011, 123, 8824; Angew. Chem., Int. Ed. 2011, 50,
8665; b) Q. Cai, S.-L. You, Org. Lett. 2012, 14, 3040; c) Q. Cai, C. Liu,
Liang, X.-W.; S.-L. You, Org. Lett. 2012, 14, 4588; d) Q. Yin, S.-L. You,
Org. Lett. 2013, 15, 4266; e) Q. Cai, Q. Yin, S.-L.You, Asian J. Org.
Chem. 2014, 3, 408; f) L. Han, C. Liu, W. Zhang, X.-X. Shi, S.-L. You,
Chem. Commun. 2014, 50, 1231; g) Q. Yin, S.-L. You, Org. Lett. 2014,
16, 2426; h) D.-H. Duan, Q. Yin, S.-G. Wang, Q. Gu, S.-L. You, Acta
Chim. Sinica 2014, 72, 1001; i) X. Zhang, W.-B. Liu, H.-F. Tu, S.-L. You,
Chem. Sci. 2015, 6, 4525.
[10] For a related elegant synthesis using chiral sulfoxide reagents, see: M.
Tayu, Y. Suzuki, K. Higuchi, T. Kawasaki, Synlett 2016, 27, 941.
[11] C. Guo, J. Song, J.-Z. Huang. P.-H. Chen, S.-W. Luo, L.-Z. Gong,
Angew. Chem. 2012, 124, 1070; Angew. Chem., Int. Ed. 2012, 51,
1046.
[5]
For selected metal-catalyzed asymmetric dearomatization of indoles,
see: a) T. Sunazuka, T. Hirose, T. Shirahata, Y. Harigaya, M. Hayashi,
K. Komiyama, S. Ōmura, A. B. Smith, III, J. Am. Chem. Soc. 2000, 122,
2122; b) B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
c) S. Sato, M. Shibuya, N. Kanoh, Y. Iwabuchi, Chem. Commun. 2009,
6264; d) Y. Lian, H. M. L. Davies, J. Am. Chem. Soc. 2010, 132, 440; e)
L. M. Repka, J. Ni, S. E. Reisman, J. Am. Chem. Soc. 2010, 132,
14418; f) N. Shimada, T. Oohara, J. Krishnamurthi, H. Nambu, S.
Hashimoto, Org. Lett. 2011, 13, 6284; g) G. Cera, M. Chiarucci, A.
Mazzanti, M. Mancinelli, M. Bandini, Org. Lett. 2012, 14, 1350; h) Y. Liu,
H. Du, Org. Lett. 2013, 15, 740; i) Y.-Q. Zhang, Y.-A. Yuan, G.-S. Liu, H.
Xu, Org. Lett. 2013, 15, 3910; j) J. E. Spangler, H. M. L. Davies, J. Am.
Chem. Soc. 2013, 135, 6802; k) H. Xiong, H. Xu, S. Liao, Z. Xie, Y.
Tang, J. Am. Chem. Soc. 2013, 135, 7851; l) M.-C. Tong, X. Chen, J. Li,
R. Huang, H. Tao, C.-J. Wang, Angew. Chem. 2014, 126, 4768; Angew.
Chem., Int. Ed. 2014, 53, 4680; m) X. Zhao, X. Liu, H. Mei, J. Guo, L.
Lin, X. Feng, Angew. Chem. 2015, 127, 4104; Angew. Chem., Int. Ed.
2015, 54, 4032; n) C. Shen, R.-R. Liu, R.-J. Fan, Y.-L. Li, T.-F. Xu, J.-R.
Gao, Y.-X. Jia, J. Am. Chem. Soc. 2015, 137, 4936.