10.1002/adsc.201701546
Advanced Synthesis & Catalysis
AD-H column (5 µm; 25 cm x 4.6 mm), λ = 254 nm, n-
hexane / isopropanol 90:10, 0.6 mL/min, column temp.:
25 °C; tR (major) = 23.0 min, tR (minor) = 32.1 min).
[9] I. Walz, A. Togni, Chem. Commun. 2008, 4315–4317.
[10] K. Yaji, M. Shindo, Synlett 2009, 2524–2528.
27
[α]D = –102 (c 1.0, CH2Cl2); 1H NMR (300 MHz,
[11] P. Cao, C. Deng, Y.-Y. Zhou, X.-L. Sun, J.-C. Zheng,
Z. Xie, Y. Tang, Angew. Chem. Int. Ed. 2010, 49,
4463–4466.
CDCl3): δ = 9.29 (br s, 1H, NH), 7.55–7.48 (m, 1H, HAr),
7.45–7.21 (m, 8H, HAr), 7.14–7.05 (m, 1H, HAr,), 5.08 (d, J
= 2.9 Hz, 1H, HAliph), 3.92 (d, J = 2.9 Hz, 1H, HAliph), 3.85
(s, 3H, CH3) ppm; 13C NMR (75 MHz, CDCl3): δ = 186.8,
169.6, 148.0, 144.6, 140.9, 137.2, 129.2 (2C), 128.3, 127.6,
127.5 (2C), 123.1, 122.4, 121.4, 113.8, 67.9, 52.9, 44.2
ppm; IR (ATR): v = 3266 (br m), 3067 (w), 3028 (w),
2950 (w), 1733 (m), 1676 (s), 1620 (w), 1541 (w), 1486
(w), 1438 (w), 1370 (w), 1320 (m), 1246 (m), 1158 (m),
1101 (w), 1063 (w), 1016 (w), 910 (w), 851 (w), 743 (m),
702 (m), 618 (w), 506 (w), 430 (w) cm–1; HRMS (ESI):
m/z calcd. for C19H15N1O3Na1 [M+Na]+: 328.0944; found:
328.0944.
[12] M. Kawatsura, K. Kajita, S. Hayase, T. Itoh, Synlett
2010, 1243–1246.
[13] G. E. Hutson, Y. E. Türkmen, V. H. Rawal, J. Am.
Chem. Soc. 2013, 135, 4988–4991.
[14] S. Raja, M. Nakajima, M. Rueping, Angew. Chem. Int.
Ed. 2015, 54, 2762–2765.
[15] K. Kitamura, N. Shimada, C. Stewart, A. C. Ateşin, T.
A. Ateşin, M. A. Tius, Angew. Chem. Int. Ed. 2015, 54,
6288–6291.
[16] Z. Xu, H. Ren, L. Wang, Y. Tang, Org. Chem. Front.
2015, 2, 811–814.
Acknowledgements
[17] T. Takeda, S. Harada, A. Nishida, Org. Lett. 2015, 17,
5184–5187.
This
work
was
supported
by
the
Deutsche
Forschungsgemeinschaft (ME 1805/11-1 and ME 1805/13-1) and
by a LOEWE research cluster (SynChemBio) of the State of
Hesse, Germany. V. A. L. thanks the RUDN University Program
5-100 for support.
[18] For organocatalytic asymmetric Nazarov cyclizations,
see: a) M. Rueping, W. Ieawsuwan, A. P. Antonchick,
B. J. Nachtsheim, Angew. Chem. Int. Ed. 2007, 46,
2097–2100; b) M. Rueping, W. Ieawsuwan, Adv. Synth.
Catal. 2009, 351, 78–84; c) W. F. Bow, A. K. Basak, A.
Jolit, D. A. Vicic, M. A. Tius, Org. Lett. 2010, 12, 440–
443; d) D. J. Kerr, B. L. Flynn, Org. Lett. 2012, 14,
1740–1743; e) A. K. Basak, N. Shimada, W. F. Bow, D.
A. Vicic, M. A. Tius, J. Am. Chem. Soc. 2010, 132,
8266–8267; f) M. Rueping, W. Ieawsuwan, Chem.
Commun. 2011, 47, 11450–11452; g) S. Raja, W.
Ieawsuwan, V. Korotkov, M. Rueping, Chem. Asian J.
2012, 7, 2361–2366; h) A. Jolit, P. M. Walleser, G. P.
A. Yap, M. A. Tius, Angew. Chem. Int. Ed. 2014, 53,
6180–6183; i) Y.-W. Huang, A. J. Frontier,
Tetrahedron Lett. 2015, 56, 3523–3526; j) A. H. Asari,
Y.-h. Lam, M. A. Tius, K. N. Houk, J. Am. Chem. Soc.
2015, 137, 13191–13199; k) J. P. Lovie-Toon, C. M.
Tram, B. L. Flynn, E. H. Krenske, ACS Catal. 2017, 7,
3466–3476; l) A. Jolit, C. F. Dickinson, K. Kitamura, P.
M. Walleser, G. P. A. Yap, M. A. Tius, Eur. J. Org.
Chem. 2017, 6067–6076.
References
[1] For reviews on the Nazarov cyclization, see: a) A. J.
Frontier, C. Collison, Tetrahedron 2005, 61, 7577–
7606; b) T. Vaidya, R. Eisenberg, A. J. Frontier,
ChemCatChem 2011, 3, 1531–1548; c) T. Itoh, T.
Nokami, M. Kawatsura, Chem. Rec. 2016, 16, 1676–
1689; d) M. G. Vinogradov, O. V. Turova, S. G. Zlotin,
Org. Biomol. Chem. 2017, 15, 8245–8269.
[2] For a review on the synthesis of chiral cyclopentenones,
see: S. P. Simeonov, J. P. M. Nunes, K. Guerra, V. B.
Kurteva, C. A. M. Afonso, Chem. Rev. 2016, 116,
5744–5893.
[3] For applications of the Nazarov cyclization for natural
product synthesis, see: a) P. E. Harrington, M. A. Tius,
J. Am. Chem. Soc. 2001, 123, 8509–8514; b) Z. Zhou,
M. A. Tius, Angew. Chem. Int. Ed. 2015, 54, 6037–
6040; c) G. Sudhakar, K. Satish, Chem. Eur. J. 2015,
21, 6475-6480; d) Z. Zhou, D. D. Dixon, A. Jolit, M. A.
Tius, Chem. Eur. J. 2016, 22, 15929–15936.
[19] For a recent report on the combination of Lewis acid
catalysis and chiral Brønsted acid catalysis, see: G.-P.
Wang, M.-Q. Chen, S.-F. Zhu, Q.-L. Zhou, Chem. Sci.
2017, 8, 7197–7202.
[4] For
a recent review on asymmetric Nazarov
cyclizations, see: N. Shimada, C. Stewart, M. A. Tius,
Tetrahedron 2011, 67, 5851–5870.
[20] For reports on iridium-catalyzed Nazarov cyclizations,
see: a) M. Janka, W. He, A. J. Frontier, R. Eisenberg, J.
Am. Chem. Soc. 2004, 126, 6864–6865; b) M. Janka, W.
He, A. J. Frontier, C. Flaschenriem, R. Eisenberg,
Tetrahedron 2005, 61, 6193–6206; c) T. Vaidya, A. C.
Atesin, I. R. Herrick, A. J. Frontier, R. Eisenberg,
Angew. Chem. Int. Ed. 2010, 49, 3363–3366; d) A. C.
Atesin, J. Zhang, T. Vaidya, W. W. Brennessel, A. J.
Frontier, R. Eisenberg, Inorg. Chem. 2010, 49, 4331–
4342.
[5] G. Liang, S. N. Gradl, D. Trauner, Org. Lett. 2003, 5,
4931–4934.
[6] V. K. Aggarwal, A. J. Belfield, Org. Lett. 2003, 5,
5075–5078.
[7] G. Liang, D. Trauner, J. Am. Chem. Soc. 2004, 126,
9544–9545.
[8] J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, J.-A. Ma,
Org. Lett. 2007, 9, 3053–3056.
7
This article is protected by copyright. All rights reserved.