Please do not adjust margins
ChemComm
Page 4 of 5
COMMUNICATION
Journal Name
Notes and references
thus use of the stoichiometric amouDnOtsI: 1o0f.1p03h9o/sCp9hCiCn0e16w79aAs
necessary to complete the reaction and to justify the
acceleration effect.
1
For selected reviews, see: (a) A. K. Sadana, R. K. Saini and W.
E. Billups, Chem. Rev., 2003, 103, 1539-1602; (b) H. Nemoto
and K. Fukumoto, Tetrahedron, 1998, 54, 5425-5464; (c) W.
Oppolzer, Synthesis, 1978, 793-802. For a computational
research, see: (d) K. Chino and T. Endo, Lett. Org. Chem.,
15 C. Lexer, D. Burtscher, B. Perner, E. Tzur, N. G. Lemcoff and C.
Slugovc, J. Organomet. Chem., 2011, 696, 2466-2470.
16 We suppose that the predominant formations of the cis-
isomers are explained by stabilized endo-transition states
2011, 8, 138-142.
2
For recent applications reported by our group, see: (a) B. Li, S.
Masuda, D. Minato, D. Zhou, K. Sugimoto, H. Nemoto and Y.
Matsuya, Tetrahedron, 2014, 70, 3981-3987; (b) K. Sugimoto,
K. Tamura, C. Tohda, N. Toyooka, H. Nemoto and Y. Matsuya,
Bioorg. Med. Chem., 2013, 21, 4459-4471; (c) Y. Matsuya, N.
Suzuki, S. Kobayashi, T. Miyahara, H. Ochiai and H. Nemoto,
Bioorg. Med. Chem., 2010, 18, 1477-1481; (d) Y. Matsuya, Y.
Imamura, T. Miyahara, H. Ochiai and H. Nemoto, Eur. J. Org.
Chem., 2008, 2008, 1426-1430; (e) Y. Matsuya, S. Masuda, T.
Itoh, T. Murai and H. Nemoto, J. Org. Chem., 2005, 70, 6898-
6903; (f) Y. Matsuya, K. Sasaki, M. Nagaoka, H. Kakuda, N.
Toyooka, N. Imanishi, H. Ochiai and H. Nemoto, J. Org. Chem.,
2004, 69, 7989-7993.
involving
p-interaction between the benzene ring and the
OQM moiety as depicted in Table 2.
17 Additional experiments regarding temperature dependency
suggested that the ring fission may occur at 0 °C (see ESI).
18 This discovery would be an important basis of a novel
modification of Staudinger-Bertozzi ligation. (a) E. Saxon and
C. R. Bertozzi, Science, 2000, 287, 2007-2010; (b) E. Saxon, J. I.
Armstrong and C. R. Bertozzi, Org. Lett., 2000, 2, 2141-2143;
(c) G. A. Lemieux, C. L. De Graffenried and C. R. Bertozzi, J.
Am. Chem. Soc., 2003, 125, 4708-4709.
3
(a) K. Yamamoto, M. F. Hentemann, J. G. Allen and S. J.
Danishefsky, Chem. Eur. J., 2003,
9, 3242-3252; (b) M. F.
Hentemann, J. G. Allen and S. J. Danishefsky, Angew. Chem.
Int. Ed., 2000, 39 1937-1940; (c) J. G. Allen, M. F.
,
Hentemann and S. J. Danishefsky, J. Am. Chem. Soc., 2000,
122, 571-575.
W. Choy and H. Yang, J. Org. Chem., 1988, 53, 5796-5798.
For a report on similar anion effects, see: T. Kametani, M.
Tsubuki, H. Nemoto and K. Suzuki, J. Am. Chem. Soc., 1981,
103, 1256-1258.
(a) Y. Matsuya, N. Ohsawa and H. Nemoto, J. Am. Chem. Soc.,
2006, 128, 13072-13073; (b) Y. Matsuya, H. Katayanagi, T.
Ohdaira, Z. L. Wei, T. Kondo and H. Nemoto, Org. Lett., 2009,
11, 1361-1364; (c) K. Sugimoto, R. Hayashi, H. Nemoto, N.
Toyooka and Y. Matsuya, Org. Lett., 2012, 14, 3510-3513.
Y. Matsuya, N. Ohsawa and H. Nemoto, J. Am. Chem. Soc.,
2006, 128, 412-413.
For reports on similar silyl effects, see: (a) M. Murakami, Y.
Miyamoto and Y. Ito, Angew. Chem. Int. Ed., 2001, 40, 189-
190; (b) M. Murakami, Y. Miyamoto and Y. Ito, J. Am. Chem.
Soc., 2001, 123, 6441-6442.
4
5
6
7
8
9
For selected reviews and references, see: (a) F. Palacios, D.
Aparicio, G. Rubiales, C. Alonso and J. de los Santos, Curr.
Org. Chem., 2006, 10, 2371-2392; (b) S. Eguchi, ARKIVOC,
2005, 98-119; (c) C. Palomo, J. Aizpurua, I. Ganboa and M.
Oiarbide, Curr. Med. Chem., 2004, 11, 1837-1872; (d) H.
Staudinger and J. Meyer, Helv. Chim. Acta, 1919, 2, 635-646;
(e) W. Q. Tian and Y. A. Wang, J. Org. Chem., 2004, 69, 4299-
4308.
10 A. S. Thompson, G. R. Humphrey, A. M. DeMarco, D. J.
Mathre and E. J. J. Grabowski, J. Org. Chem., 1993, 58, 5886-
5888.
11 Facile ring cleavage of BCBs was suggested in the presence of
amino-substituents, see: (a) M. W. Hanna and S. W. Fenton, J.
Org. Chem., 1961, 26, 1371-1374; (b) M. Chaumontet, R.
Piccardi and O. Baudoin, Angew. Chem. Int. Ed., 2009, 48
179-182.
,
12 (a) W. R. Dolbier, H. Koroniak, K. N. Houk and C. Sheu, Acc.
Chem. Res., 1996, 29, 471-477; (b) S. Niwayama, E. A. Kallel,
D. C. Spellmeyer, C. Sheu and K. N. Houk, J. Org. Chem., 1996,
61, 2813-2825; (c) C. W. Jefford, G. Bernardinelli, Y. Wang,
D. C. Spellmeyer, A. Buda and K. N. Houk, J. Am. Chem. Soc.,
1992, 114, 1157-1165; (d) P. S. Lee, X. Zhang and K. N. Houk,
J. Am. Chem. Soc., 2003, 125, 5072-5079.
13 A similar 1,5-prototropy of OQM derivatives was reported
under thermal conditions, see: K. Iida, K. Komada, M. Saito
and M. Yoshioka, J. Org. Chem., 1999, 64, 7407-7411.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins