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S. Kamijo et al.
Paper
Synthesis
6f
López, Ó. Synthesis 2007, 1589. (c) Baskin, J. M.; Bertozzi, C. R.
Aldrichimica Acta 2010, 43, 15. (d) Thirumurugan, P.; Matosiuk,
D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.
Colorless solid; mp 160.8–161.6 °C.
IR (ATR, neat): 3420, 3102, 3069, 2950, 2919, 2866, 1664, 1515, 1348,
(5) (a) Sandler, S. R.; Karo, W. Organic Functional Group Prepara-
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1335.
851, 714 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 1.41 (m, 2 H), 1.48–1.75 (m, 11 H), 1.96
(m, 2 H), 2.02–2.20 (m, 2 H), 5.88 (br s, 1 H), 7.87 (d, J = 8.7 Hz, 2 H),
8.27 (d, J = 8.7 Hz, 2 H).
13C NMR (125 MHz, CDCl3): δ (detectable signals) = 22.3, 27.5, 38.8,
57.8, 123.7, 127.7, 141.9, 149.2, 164.5; two signals in the cyclohexane
ring are probably missing due to the rapid ring-flip of the cis-decalin
core.
HRMS (APCI): m/z [M + H]+ calcd for C17H23N2O3: 303.1703; found:
303.1716.
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ing hydroxy groups of tertiary alcohols, see: Dryzhakov, M.;
Hellal, M.; Wolf, E.; Falk, F. C.; Moran, J. J. Am. Chem. Soc. 2015,
137, 9555.
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6f′12
[CAS Reg. No. 1654756-89-4]
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1081. (b) Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.;
Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am.
Colorless solid; mp 191.1–192.6 °C.
1H NMR (500 MHz, CDCl3): δ = 1.10–1.28 (m, 4 H), 1.31–1.48 (m, 4 H),
1.49–1.62 (m, 5 H), 1.72–1.78 (m, 2 H), 2.76–2.83 (m, 2 H), 5.74 (br s,
1 H), 7.90 (d, J = 8.8 Hz, 2 H), 8.30 (d, J = 8.8 Hz, 2 H).
13C NMR (125 MHz, CDCl3): δ = 21.6, 25.9, 28.8, 34.3, 45.3, 56.9, 123.9,
127.7, 141.9, 149.3, 164.4.
Chem. Soc. 1996, 118, 5192. For
a related report, see:
(c) Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115,
9347.
(12) Sharma, A.; Hartwig, J. F. Nature 2015, 517, 600.
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137, 5300.
HRMS (APCI): m/z [M + H]+ calcd for C17H23N2O3: 303.1703; found:
303.1701.
(14) For related examples from our group, see: (a) Kamijo, S.;
Hoshikawa, T.; Inoue, M. Tetrahedron Lett. 2010, 51, 872.
(b) Kamijo, S.; Hoshikawa, T.; Inoue, M. Tetrahedron Lett. 2011,
52, 2885. (c) Kamijo, S.; Hoshikawa, T.; Inoue, M. Org. Lett. 2011,
13, 5928. (d) Hoshikawa, T.; Kamijo, S.; Inoue, M. Org. Biomol.
Chem. 2013, 11, 164. (e) Hoshikawa, T.; Yoshioka, S.; Kamijo, S.;
Inoue, M. Synthesis 2013, 45, 874. (f) Amaoka, Y.; Nagatomo, M.;
Watanabe, M.; Tao, K.; Kamijo, S.; Inoue, M. Chem. Sci. 2014, 5,
4339. (g) Kamijo, S.; Hirota, M.; Tao, K.; Watanabe, M.; Murafuji,
T. Tetrahedron Lett. 2014, 55, 5551. (h) Kamijo, S.; Tao, K.; Takao,
G.; Murooka, H.; Murafuji, T. Tetrahedron Lett. 2015, 56, 1904.
(i) Kamijo, S.; Tao, K.; Takao, G.; Tonoda, H.; Murafuji, T. Org. Lett.
2015, 17, 3326.
(15) For recent related transformations from other groups, see:
(a) Kee, C. W.; Chin, K. F.; Wong, M. W.; Tan, C.-H. Chem.
Commun. 2014, 50, 8211. (b) Xia, J.-B.; Zhu, C.; Chen, C. Chem.
Commun. 2014, 50, 11701. (c) Cantillo, D.; de Frutos, O.; Rincón,
J. A.; Mateos, C.; Kappe, C. O. J. Org. Chem. 2014, 79, 8486.
(d) Xia, J.-B.; Zhu, C.; Chen, C. J. Am. Chem. Soc. 2013, 135, 17494.
(e) Hoshikawa, T.; Inoue, M. Chem. Sci. 2013, 4, 3118.
Acknowledgment
This research was supported by a Grant-in-Aid for Scientific Research
on Innovative Areas ‘Advanced Molecular Transformations by Organo-
catalysts’ (MEXT, Japan) and a Program to Disseminate Tenure Track-
ing System (MEXT, Japan) to S.K.
Supporting Information
Supporting information for this article is available online at
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, 115–121