Journal of the American Chemical Society
Page 4 of 5
The authors declare no competing financial interests.
AUTHOR INFORMATION
1
2
3
4
Corresponding Author
ACKNOWLEDGMENT
Funding of this work by the NIH (GM093930) is gratefully
acknowledged.
Notes
5
6
7
8
9
A. G. ACS Comb. Sci. 2013, 15, 73-76. (c) Kumar, N. N. B.; Mukhina, O.
A.; Kutateladze, A. G. J. Am. Chem. Soc., 2013, 135, 9608-9611. (d) Cronk,
W.C.; Mukhina, O.A.; Kutateladze, A.G. J. Org. Chem., 2014, 79, 1235-
1246. (e) Kumar, N.N.B.; Kuznetsov, D.M.; Kutateladze, A.G. Org. Lett.,
2015, 17, 438-441. (f) Mukhina, O.A.; Kumar, N.N.B.; Cowger, T.M.;
Kutateladze, A.G. J. Org. Chem., 2014, 79, 10956-10971. (g) Umstead,
W.J.; Mukhina, O.A.; Kutateladze, A.G. Eur. J. Org. Chem., 2015, 2205-
2213. (h) Umstead, W.J.; Mukhina, O.A.; Kutateladze, A.G. Aust. J. Chem.
2015, 68, 1672-1681.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
REFERENCES
(1) For reviews, see (a) Rau, H. Chem. Rev., 1983, 83, 535-547. (b) Inoue,
Y.; Ramamurthy, V., Ed. Chiral Photochemistry, Marcel Dekker, New
York, 2004, 665 p. (c) Grosch, B.; Bach, T. Enantioselective Photocycload-
dition Reactions in Solution CRC Handbook on Photochemistry and Pho-
tobiology 2nd edition Ed. Horspool, W.; Lenci, F. CRC Press, 2003, p. 61-1
(d) Natarajan, A.; Kaanumalle L.S.; Ramamurthy, V. Manipulating Photo-
chemical Reactions CRC Handbook on Photochemistry and Photobiology
2nd edition Ed. Horspool, W.; Lenci, F. CRC Press, 2003, p. 107-1 (e) Bach,
T. Synthesis 1998, 683-703. (f) Namyslo, J. C.; Kaufmann, D. E. Chem.
Rev. 2003, 103, 1485-1538. (g) Lee-Ruff, E.; Mladenova, G. Chem. Rev.
Bach, Angew. Chem. Int. Ed. 2015, 54, 3872-3890.
(2) (a) Terao, K.; Nishiyama, Y.; Kakiuchi, K. J. Flow Chem. 2014, 4, 35-
39. (b) Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc.
2002, 124, 7982-7990. (c) Bach, T.; Bergmann, H.; Harms, K. J. Am.
Chem. Soc., 1999, 121, 10650-10651. (d) Bach, T.; Bergmann, H.;
Brummerhop, H.; Lewis, W.; Harms, K. Chem. Eur. J., 2001, 7, 4512-
4521.
(3) For recent examples, see (a) Vallavoju, N.; Selvakumar, S.; Jockusch,
S.; Sibi, M.P.; Sivaguru, J. Angew. Chem. Int. Ed. 2014, 53, 5604-5608.
(b) Coote, S.C.; Pöthig, A.; Bach, T. Chem. Eur. J. 2015, 21, 6906-6912.
(c) Brimoulle, R.; Bauer, A.; Bach, T. J. Am. Chem. Soc., 2015, 137,
5170-5176. (d) Yanagisawa, Y.; Nishiyama, Y.; Tanimoto, H.; Morimoto,
T. Kakiuchi, K. Tetrahedron Lett., 2014, 55, 2123-2126. (e) Zhao, G.;
Yang, C.; Sun, H.; Lin, R.; Xia, W. Org. Lett., 2012, 14, 776-779. (f)
Faure, S.; Piva-Le-Blanc, S.; Bertrand, C.; Pete, J.-P.; Faure, R.; Piva, O.
J. Org. Chem. 2002, 67, 1061-1070.
(4) [4+2] cycloadditions: (a) Grosch, B.; Orlebar, C.N.; Herdtweck, E.;
Kaneda, M.; Wada, T.; Inoue, Y.; Bach, T. Chem. Eur. J. 2004, 10, 2179-
2189. (b) Kim, J.-I.; Schuster, G.B. J. Am. Chem. Soc., 1992, 114, 9309-
9317. (c) Asaoka, S.; Ooi, M.; Jiang, P.; Wada, T.; Inoue, Y. J. Chem. Soc.,
Perkin Trans. 2, 2000, 77-84. [3+2] Cycloadditions: (d) Lajkiewicz, N. J.;
Roche, S.P.; Gerard, B.; Porco, J.A. J. Am. Chem. Soc., 2012, 134, 13108-
13113. (e) Sugimura, T.; Nishiyama, N.; Tai, A.; Hakushi, T. Tetrahedron:
Asymmetry 1994, 5, 1163-1166. [4+4] Cycloadditions: (f) Bach, T.; Berg-
mann, H.; Grosch, B.; Harms, K. Org. Lett., 2001, 3, 601-603. Photodecon-
jugation reactions: (g) Henin, F.; Letinois, S.; Muzart, J. Tetrahedron:
Asymmetry, 2000, 11, 2037-2044. Electrocyclizations: (h) Naito, Y.; Tada,
Y.; Ninomiya, I. Heterocycles, 1984, 22, 237-240. (i) Bach, T.; Grosch, B.;
Strassner, T.; Herdtweck, E. J. Org. Chem. 2003, 68, 1107-1116.
(5) (a) Nicewicz, D.A.; MacMillan, D.W. C. Science 2008, 322, 77-80. (b)
Nagib, D.A.; Scott, M.E.; MacMillan, D.W.C. J. Am. Chem. Soc., 2009,
131, 10875-10877. (c) Cherevatskaya, M.; Neumann, M.; Füldner, S.; Har-
lander, C.; Kümmel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; König,
B. Angew. Chem., Int. Ed. 2012, 51, 4062-4066. (d) DiRocco, D. A.;
Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094-8097. (e) Cecere, G.; König,
C. M.; Alleva, J. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135,
11521-11524. (f) Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M.
F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735-17738. (g) Ber-
gonzini, G.; Schindler, C. S.; Wallentin, C.-J.; Jacobsen, E. N.; Stephenson,
C. R. J. Chem. Sci. 2014, 5, 112-116. (h) Du, J.; Skubi, K. L.; Schultz, D.
M.; Yoon, T. P. Science 2014, 344, 392-396. (i) Tellis, J. C.; Primer, D. N.;
Molander, G. A. Science 2014, 345, 433-436. (j) Zhu, Y.; Zhang, L.; Luo,
S. J. Am. Chem. Soc. 2014, 136, 14642-14645. (k) Huo, H.; Shen, X.;
(7) Mukhina, O.A.; Kuznetsov, D.M.; Cowger, T.M.; Kutateladze, A.G.
Angew. Chem. Int. Ed., 2015, 39, 11516-11520.
(8) For selected examples, see (a) Meyers, A.I.; Knaus, G.; Kamata, K.;
Ford, M.E. J. Am. Chem. Soc., 1976, 98, 567-576. (b) Meyers, A.I.; Whit-
ten, C.E. J. Am. Chem. Soc. 1975, 97, 6266-6267. (c) Meyers, A.I.; Ship-
man, N. J. Org. Chem. 1991, 56, 7098-7102. (d) Michelon, F.; Pouihes, A.;
van Bac, N.; Langlois, N. Tetrahedron Lett. 1992, 33, 1743-1746. (e) Da-
huron, N.; Langlois, N. Synlett, 1996, 51-52. (f) Johnson, J. A.; Li, N.;
Sames, D. J. Am. Chem. Soc. 2002, 124, 6900-6903. (g) Giri, R.; Chen, X.;
Yu, J.-Q. Angew. Chem. Int. Ed. 2005, 44, 2112-2115. For reviews, see (h)
Meyers, A.I. J. Org. Chem. 2005, 70, 6137-6151. (i) Gnas, Y.; Glorius, F.
Synthesis, 2006, 1899-1930. (j) Ager, D.J.; Prakash, I.; Schaad, D.R. Chem.
Rev., 1996, 96, 835-876.
(9) For reviews, see (a) Hargaden, G.C.; Guiry, P.J. Chem. Rev. 2009, 109,
2505-2550. (b) Gossage, R.A. Dalton Trans., 2011, 40, 8755-8759. (c)
Ward, B.D.; Gade, L.H. Chem. Commun., 2012, 48, 10587-10599. For a
recent example, see: (d) Chu, J.C.K.; Dalton, D.M.; Rovis, T. J. Am. Chem.
Soc. 2015, 137, 4445-4452.
(10) (a) Rajaram, S.; Sigman, M. S. Org. Lett. 2002, 4, 3399-3401. (b) Ra-
jaram, S.; Sigman, M.S. Org. Lett., 2005, 7, 5473-5475. (c) Jensen, K. H.;
Sigman, M. S. Angew. Chem., Int. Ed. 2007, 46, 4748-4750. (d) Harper,
K.C.; Sigman, M.S. J. Org. Chem. 2013, 78, 2813-2818.
(11) (a) Henary, M.M., Wu, Y.; Cody, J.; Sumalekshmy, S.; Li, J.; Mandal,
S.; Fahrni, C.J. J. Org. Chem. 2007, 72, 4784-4797. (b) Hsieh, C.-C.;
Cheng, Y.-M.; Hsu, C.-J.; Chen, K.-Y.; Chou, P.T. J. Phys.Chem. A 2008,
112, 8323-8332. (c) Chen, W.-H., Pang, Y. Tetrahedron Lett., 2010, 51,
1914-1918. (d) Santos, F.S.; Costa, T.M.H.; Stefani, W.; Gonçalves, P.F.B.;
Descalzo, R.R.; Benvenutti. E.V.; Rodembusch, F.S. J. Phys. Chem. A
2011, 115, 13390-13398. (e) Patil, V.S.; Padalkar, V.S.; Tathe, A.B.; Gupta,
V.D.; Sekar, N. J. Fluoresc, 2013, 23, 1019-1029.
(12) Chen, W.-H.; Xing, Y.; Pang, Y. Org. Lett. 2011, 13, 1362-1365.
(13) Yang, P.; Zhao, J.; Wu, W.; Yu, X.; Liu, Y. J. Org. Chem., 2012, 77,
6166-6178.
(14) Tseng, H.W.; Liu,J.-Q.; Chen, Y.An.; Chao, C.-M.; Liu, K.-M.;Chen,
C.-L.; Lin, T-C.; Hung, C.-H.; Chou, Y.-L.; Lin, T.-C.; Wang, T.-L.;
Chou,P.-T. Phys. Chem. Lett. 2015, 6, 1477-1486.
(15) In the reactions shown in Scheme 2 the minor [4+2] product was not
isolated.
(16) (a) Zhang, Z.; Lippert, K. M.; Hausmann, H.; Kotke, M.; Schreiner, P.
R. J. Org. Chem. 2011, 76, 9764-9776. (b) Kurosu, M.; Lin, M.-H.; Kishi,
Y. J. Am. Chem. Soc., 2004, 126, 12248-12249.
(17) Synthesized analogously to Thérien, M.-É.; Guilbault, A.-A.; Legault,
C.Y. Tetrahedron: Asymmetry, 2013, 24, 1193-1197.
(18) Mukhina, O.A.; Cronk, W.C.; Kumar, N.N.B.; Sekhar, M.; Samanta,
A.; Kutateladze, A.G. J. Phys. Chem. A., 2014, 118, 10487-10496.
Wang, C.; Zhang, L.; Röse, P.; Chen, L.-A.; Harms, K.; Marsch, M.; Hilt,
G.; Meggers, E. Nature 2014, 515, 100-103. (l) Gutierrez, O.; Tellis, J. C.;
Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015,
137, 4896-4899. (m) Huo, H.; Wang, C.; Harms, K.; Meggers E. J. Am.
Chem. Soc., 2015, 137, 9551-9554.
(6) (a) Mukhina, O. A.; Kumar, N. N. B.; Arisco, T. M.; Valiulin, R. A.;
Metzel, G. A.; Kutateladze, A. G. Angew. Chem., Int. Ed. 2011, 50, 9423-
9428. (b) Nandurkar, N. S.; Kumar, N. N. B.; Mukhina, O. A.; Kutateladze,
4
ACS Paragon Plus Environment