10.1002/anie.201705746
Angewandte Chemie International Edition
COMMUNICATION
L. L. Lin, X. H. Liu, X. M. Feng, Angew. Chem. 2010, 122, 3887; Angew.
Chem. Int. Ed. 2010, 49, 3799; f) C. Wang, Z. Y. Han, H.W. Luo, L. Z.
Gong, Org. Lett. 2010, 12, 2266; g) A H. Xu, S. J. Zuend, M. G. Woll, Y.
Tao, E. N. Jacobsen, Science, 2010, 327, 986; h) G. Bergonzini, L.
Gramigna, A. Mazzanti, M. Fochi, L. Bernardi, A. Ricci, Chem. Commun.
2010, 46, 327; i) G. Dagousset, J. P. Zhu, G. Masson, J. Am. Chem. Soc.
2011, 133, 14804; j) M. S. Xie, X. H. Liu, Y. Zhu, X. H. Zhao, Y. Xia, L. L.
Lin, X. M. Feng, Chem. Eur. J. 2011, 17, 13800; k) J. H. Lin, G. Q. Zong,
R. B. Du, J. C. Xiao, S. B. Liu, Chem. Commun. 2012, 48, 7738; l) G.
Dagousset, P. Retailleau, G. Masson, J. P. Zhu, Chem. Eur. J. 2012, 18,
5869; m) L. He, M. Bekkaye, P. Retailleau, G. Masson, Org. Lett. 2012,
14, 3158; n) F. Shi, G.-J. Xing, Z.-L. Tao, S.-W. Luo, S.-J. Tu, L.-Z. Gong,
J. Org. Chem. 2012, 77, 6970; o) F. Shi, G. J. Xing, R. Y. Zhu, W. Tan,
S. J. Tu, Org. Lett. 2013, 15, 128; p) C. Min, N. Mittal, D. X. Sun, D.
Seidel, Angew. Chem. 2013, 125, 14334; Angew. Chem. Int. Ed. 2013,
52, 14084; q) L. Caruana, M. Fochi, S. Ranieri, A. Mazzanti, L. Bernardi,
Chem. Commun. 2013, 49, 880; r) D. Huang, F. Xu, T. Chen, Y. Wang,
X. Lin, RSC Advances 2013, 3, 573; s) Z. L. Chen, B. L. Wang, Z. B.
Wang, G. Y. Zhu, J. W. Sun, Angew. Chem. 2013, 125, 2081; Angew.
Chem. Int. Ed. 2013, 52, 2027; t) C. S. Luo, Y. Huang, J. Am. Chem. Soc.
2013, 135, 8193; u) J. Brioche, T. Courant, L. Alcaraz, M. Stocks, M.
Furber, J. Zhu, G. Masson, Adv. Synth. Catal. 2014, 356, 1719; v) J. Yu,
H.-J. Jiang, Y. Zhou, S.-W. Luo, L.-Z Gong, Angew. Chem. 2015, 127,
11361 Angew. Chem. Int. Ed. 2015, 54, 11209; w) X.-L. Yu, L. Kuang, S.
Chen, X.-L. Zhu, Z.-L. Li, B. Tan, X.-Y. Liu, ACS Catal. 2016, 6, 6182; x)
W. Dai, X.-L. Jiang, J.-Y. Tao, F. Shi, J. Org. Chem. 2016, 81, 185.
[3]
[4]
M. Fochi, L. Caruana, L. Bernardi, Synthesis 2003, 46, 135.
Selected Examples of diastereoselective intramolecular Povarov
reaction: a) F. Linkert, S. Laschat, Synlett 1994, 125; b) A. S. Kiselyov,
L. Smith, R. W. Armstrong, Tetrahedron 1998, 54, 5089; c) G. Sabitha,
E. V. Reddy, J. S. Yadav, Synthesis 2002, 409; d) N. A. Magomedov,
Org. Lett. 2003, 5, 2509; e) G. Dickmeiss, K. L. Jensen, D. Worgull, P. T.
Franke, K. A. Jørgensen, Angew. Chem. 2011, 123, 1618; Angew. Chem.
Int. Ed. 2011, 50, 1580; f) H. Wu, Y.-M. Wang, Chem. Eur. J. 2014, 20,
5899; g) H.-G. Imrich, J. Conrad, U. Beifuss, Eur. J. Org. 2016, 5706
a) C. Min, C.-T. Lin, D. Seidel, Angew. Chem. 2015, 127, 6708; Angew.
Chem. Int. Ed. 2015, 54, 6608; b) C. Min, D. Seidel, Chem. Eur. J. 2016,
22, 10817.
[5]
[6]
a) L. He, G. Laurent, P. Retailleau, B. Folléas, J.-L. Brayer, G. Masson,
Angew. Chem. 2013, 125, 11294; Angew. Chem. Int. Ed. 2013, 52,
11088; b) J. Pous, T. Courant, G. Bernadat, B.I. Iorga, F. Blanchard, G.
Masson, J. Am. Chem. Soc. 2015, 137, 11950; c) A. Dumoulin, G.
Masson, J. Org. Chem. 2016, 81, 10154.
[7]
For recent reviews on chiral phosphoric acid catalysis, see: a) T.
Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999; b) T.
Akiyama, Chem. Rev. 2007, 107, 5744; c) M. Terada, Chem. Commun.
2008, 4097; d) M. Terada, Synthesis 2010, 1929; e) M. Terada, Bull.
Chem. Soc. Jpn. 2010, 83, 101; f) D. Kampen, C. M. Reisinger, B. List,
Top. Curr. Chem. 2010, 291, 395; g) S. Schenker, A. Zamfir, M. Freund,
S. B. Tsogoeva, Eur. J. Org. Chem. 2011, 2209; h) M. Rueping, A.
Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539; i) D. Parmar, E.
Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047; also, see:
j) T. Akiyama; K. Mori, Chem. Rev. 2015, 115, 9277.
[8]
[9]
We thank the referee for suggesting that the precipitation of 4 might
prevent the product inhibition and thus favoring the catalyst turnover as
well as bringing to our attention ref 9.
L. Li, M. Ganesh, D. Seidel, J. Am. Chem. Soc. 2009, 131, 11648.
[10] For the reason of simplicity of protocol, 1 mol % instead of 0,2 mol % of
TRIP 3 was used. 32.
[11] M. Abelman, R. Jiang, J. Zablocki, D. Koltun, (CV Therapeutics, Inc.)
ABCA1 elevating compounds. US Patent 2007/10544 A1, January 11,
2007.
[12] No nonlinear effect was observed confirming that only
a single
phosphoric acid catalyst activates the cyclization substrate (see
supporting information).
[13] A. Váradi, T. C. Palmer, P. R. Notis, G. N. Redel-Traub, D. Afonin, J. J.
Subrath, G. W. Pasternak, C. Hu, I. Sharma, S. Majumdar, Org. Lett.
2014, 16, 1668.
[14] A. Keßberg, P. Metz, Org. Lett. 2016, 18, 6500.
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