Y. Yoshida et al. / Tetrahedron Letters 52 (2011) 6877–6879
6879
nHex
N
LiN(SO CF )
2
3 2
N
nBuI (5 eq)
*
N
(2.2 eq)
N
( )-1n
( )-1p
N
MeCN, reflux
MeOH, rt
N
1
.4 mmol scale:
0.84 mmol scale:
quant (1.04 g)
Tg = 18 C
(
)-5b
nHex
9
4% (975 mg)
o
o
T g = 17 C
Scheme 3. Synthesis of optically pure spiro triazolium salts 1.
2
010, 2659, 21; Xu, D.-Z.; Liu, Y.; Shi, S.; Wang, Y. Tetrahedron: Asymmetry 2010,
Acknowledgments
2
530, 21; (q) Wang, W.-H.; Wang, X.-B.; Kodama, K.; Hirose, T.; Zhang, G.-Y.
Tetrahedron 2010, 66, 4970; (r) Qian, Y.; Zheng, X.; Wang, Y. Eur. J. Org. Chem.
2010, 3672; (s) Zheng, X.; Qian, Y.-B.; Wang, Y. Eur. J. Org. Chem. 2010, 515; (t)
Maltsev, O. V.; Chizhov, A. O.; Zlotin, S. G. Chem. Eur. J. 2011, 17, 6109; (u)
Larionova, N. A.; Kucherenko, A. S.; Siyutkin, D. E.; Zlotin, S. G. Tetrahedron
This work was supported by a Grant-in-Aid for Scientific Re-
search from the Ministry of Education, Culture, Sports, Science
and Technology, Japan. We thank the technical staff of the ISIR
Comprehensive Analysis Center at Osaka University.
2011, 67, 1948; (v) Cybulski, J.; Wisniewska, A.; Kulig-Adamiak, A.; Dabrowski,
Z.; Praczyk, T.; Michalczyk, A.; Walkiewicz, F.; Materna, K.; Pernak, J.
Tetrahedron Lett. 2011, 52, 1325.
4
5
6
.
.
.
(a) Howarth, J.; Hanlon, K.; Fayne, D.; McCormac, P. Tetrahedron Lett. 1997, 38,
Supplementary data
3097; (b) Pegot, B.; Vo-Thanh, G.; Gori, D.; Loupy, A. Tetrahedron Lett. 2004, 45,
6425; (c) Ding, J.; Desikan, V.; Han, X.; Xiao, T. L.; Ding, R.; Jenks, W. S.;
Armstrong, D. W. Org. Lett. 2005, 7, 335; (d) Wang, Z.; Wang, Q.; Zhang, Y.; Bao,
W. Tetrahedron Lett. 2005, 46, 4657; Biedron, T.; Kubisa, P. J. Polym. Sci. Part A:
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