Communication
ChemComm
4 For selected reviews, see: (a) G. Casiraghi, F. Zanardi, G. Appendino
and G. Rassu, Chem. Rev., 2000, 100, 1929; (b) S. E. Denmark,
J. R. Heemstra Jr and G. L. Beutner, Angew. Chem., Int. Ed., 2005,
44, 4682; (c) G. Casiraghi, L. Battistini, C. Curti, G. Rassu and
F. Zanardi, Chem. Rev., 2011, 111, 3076; (d) S. V. Pansare and
E. K. Paul, Chem. – Eur. J., 2011, 17, 8770.
5 For selected reviews, see: (a) C. Schneider and F. Abels, Org. Biomol.
Chem., 2014, 12, 3531; (b) Y. L. Yin and Z. Y. Jiang, ChemCatChem,
2017, 9, 4306For selected examples, see: (c) B. Zhu, B. Lu, H. Zhang,
X. Xu, Z. Jiang and J. Chang, Org. Lett., 2019, 21, 3271; (d) B.-X. Xiao,
C.-H. Shi, S.-Y. Liang, B. Jiang, W. Du and Y.-C. Chen, Org. Lett.,
2019, 21, 7554; (e) Z.-H. Wang, X.-Y. Zhang, C.-W. Lei, J.-Q. Zhao,
Y. You and W.-C. Yuan, Chem. Commun., 2019, 55, 9327; ( f ) W. Lin,
X. Lin, Y. Cheng, X. Chang, S. Zhou, P. Li and W. Li, Org. Chem.
Front., 2019, 6, 2452.
6 For selected examples of vinylogous Michael reaction via asym-
metric iminium activation, see: (a) W. Xie, L. Yue, D. Xue,
X. L. Ma, Y. C. Chen, Y. Wu, J. Zhu and J. G. Deng, Chem. Commun.,
2006, 1563; (b) J. W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue,
Y. C. Chen, Y. Wu, J. Zhu and J. G. Deng, Angew. Chem., Int. Ed.,
2007, 46, 389; (c) J. Lu, F. Liu and T.-P. Loh, Adv. Synth. Catal., 2008,
350, 1781; (d) J. Lu, F. Liu, W. J. Zhou and T. P. Loh, Tetrahedron
Lett., 2008, 49, 5389.
7 (a) D. Xue, Y. C. Chen, Q. W. Wang, L. F. Cun, J. Zhu and J. G. Deng,
Org. Lett., 2005, 7, 5293; (b) T. Y. Liu, H. L. Cui, J. Long, B. J. Li,
Y. Wu, L. S. Ding and Y. C. Chen, J. Am. Chem. Soc., 2007, 129, 1878;
(c) B. Niess and K. A. Jørgensen, Chem. Commun., 2007, 1620;
(d) J. Aleman, C. B. Jacobsen, K. Frisch, J. Overgaard and
K. A. Jørgensen, Chem. Commun., 2008, 632; (e) J. Lu, W. J. Zhou,
F. Liu and T. P. Loh, Adv. Synth. Catal., 2008, 350, 1796; ( f )
X.-L. Zhu, W.-J. He, L.-L. Yu, C.-W. Cai, Z.-L. Zuo, D.-B. Qin,
Q.-Z. Liu and L.-H. Jing, Adv. Synth. Catal., 2012, 354, 2965;
(g) S. Rout, S. K. Ray, R. A. Unhale and V. K. Singh, Org. Lett.,
2014, 16, 5568; (h) X. Li, X. Xu, W. Wei, A. Lin and H. Yao, Org. Lett.,
2016, 18, 428.
product 6a was assigned by means of TD-DFT calculations of
the electronic circular dichroism (ECD) spectra (see the ESI,†
for details). The stereochemistry of the remaining products 4
and 6 was assigned analogously.
In summary, we have developed an efficient asymmetric orga-
nocatalytic triple-cascade reaction, which was initiated by the viny-
logous Michael reaction between 2-hydroxycinnamaldehydes and
either acyclic or cyclic ketone-derived a,a-dicyanoalkenes under
iminium ion activation, followed by oxa-Michael reaction and
aldol-type reaction sequence, yielding the methylene-bridged
benzofused oxabicyclo[3.3.1]nonane derivatives bearing one
oxa-quaternary stereocenter in good yields with excellent stereo-
selectivities. It should be noted that, although both 2-hydro-
xycinnamaldehydes and a,a-dicyanoalkenes exhibited multisite
reactivities in the reaction process, only one of the three possible
reaction pathways worked, which could be smoothly scaled up
even at low catalyst loading (as low as 0.5 mol%), affording
similar good results. Further applications of this methodology
with other vinylogous substrates are under investigation.
We acknowledge the National Science and Technology
Major Project for Significant New Drugs Development (No.
2018ZX09735004), the Scientific and Technological Innovation
Project financially supported by the Qingdao National Labora-
tory for Marine Science and Technology (No. 2015ASKJ02-06),
and the NSFC-Shandong Joint Fund for Marine Science
Research Centers (No. U1606403) for financial support.
8 (a) H. L. Cui, J. Peng, X. Feng, W. Du, K. Jiang and Y. C. Chen,
Chem. – Eur. J., 2009, 15, 1574; (b) J. W. Xie, W. Chen, R. Li, M. Zeng,
W. Du, L. Yue, Y. C. Chen, Y. Wu, J. Zhu and J. G. Deng, Angew.
Chem., Int. Ed., 2007, 46, 389; (c) T. R. Kang, J. W. Xie, W. Du, X. Feng
and Y. C. Chen, Org. Biomol. Chem., 2008, 6, 2673; (d) Z. W. Guo,
X. S. Li, W. D. Zhu and J. W. Xie, Eur. J. Org. Chem., 2012, 6924;
(e) X. M. Shi, W. P. Dong, L. P. Zhu, X. X. Jiang and R. Wang, Adv.
Synth. Catal., 2013, 355, 3119; ( f ) X. F. Huang, Y. F. Zhang, Z. H. Qi,
N. K. Li, Z. C. Geng, K. Li and X. W. Wang, Org. Biomol. Chem., 2014,
12, 4372; (g) S. Meninno, A. Mazzanti and A. Lattanzi, Adv. Synth.
Catal., 2018, 361, 79.
9 (a) X.-J. Lv, Y.-H. Chen and Y.-K. Liu, Org. Lett., 2019, 21, 190;
(b) C. Wang, Y.-H. Chen, H.-C. Wu, C. Wang and Y.-K. Liu, Org. Lett.,
2019, 21, 6750; (c) X.-Q. Zhang, X.-J. Lv, J.-P. Pei, R. Tan and
Y.-K. Liu, Org. Chem. Front., 2020, 7, 292.
10 (a) Z.-H. You, Y.-H. Chen, Y. Tang and Y.-K. Liu, Org. Lett., 2018,
20, 6682; (b) Y.-H. Chen, X.-J. Lv, Z.-H. You and Y.-K. Liu, Org. Chem.
Front., 2019, 6, 3725; (c) Y.-H. Chen, X.-J. Lv, Z.-H. You and Y.-K. Liu,
Org. Lett., 2019, 21, 5556.
Conflicts of interest
There are no conflicts to declare.
Notes and references
1 (a) A. T. McPhail, T.-S. Wu, T. Ohta and H. Furukawa, Tetrahedron
Lett., 1983, 24, 5377; (b) T.-S. Wu, M.-L. Wang, P.-L. Wu and
T.-T. Jong, Phytochemistry, 1995, 40, 1817; (c) B. Portet, N. Fabre,
V. Roumy, H. Gornitzka, G. Bourdy, S. Chevalley, M. Sauvain,
A. Valentin and C. Moulis, Phytochemistry, 2007, 68, 1312;
(d) S. A. T. Fobofou, K. Franke, G. Sanna, A. Porzel, E. Bullita,
P. L. Colla and L. A. Wessjohann, Bioorg. Med. Chem., 2015, 23, 6327.
2 (a) D. F. Yu, Y. Wang and P. F. Xu, Adv. Synth. Catal., 2011, 353, 2960;
(b) D. H. Dethe and B. D. Dherange, J. Org. Chem., 2015, 80, 4526;
(c) K. Yoshida, Y. Fujino, Y. Takamatsu, K. Matsui, A. Ogura,
Y. Fukami, S. Kitagaki and K.-I. Takao, Org. Lett., 2018, 20, 5044.
3 For selected reviews, see: (a) R. C. FusoN, Chem. Rev., 1935, 16, 1;
11 (a) L. Zu, S. Zhang, H. Xie and W. Wang, Org. Lett., 2009, 11, 1627;
(b) D. B. Ramachary, M. S. Prasad, S. Vijaya Laxmi and
R. Madhavachary, Org. Biomol. Chem., 2014, 12, 574.
´
(b) R. Chinchilla and C. Najera, Chem. Rev., 2000, 100, 1891; (c) H. Li
and L. Yin, Tetrahedron Lett., 2018, 59, 4121; (d) B.-X. Xiao, X.-Y. Gao,
W. Du and Y.-C. Chen, Chem. – Eur. J., 2019, 25, 1607; (e) C. Curti,
L. Battistini, A. Sartori and F. Zanardi, Chem. Rev., 2020, 120, 2448. 12 See the ESI† for full optimization studies.
This journal is The Royal Society of Chemistry 2021
Chem. Commun., 2021, 57, 1762ꢀ1765 | 1765