10.1002/cctc.201700281
ChemCatChem
COMMUNICATION
ether) and the pressure was slowly increased to 9 kbar at ambient
temperature (20−25 °C) by hexane compressing. After the pressure was
stabilized, the reaction mixture was kept under these conditions for 20 h.
After decompression, the reaction mixture was concentrated and
chromatographed on a silica gel to afford tertiary αꢀtrifluoromethyl
alcohols 4.
[8]
[9]
a) P. Kwiatkowski, K. Dudziński D. Łyżwa, Org. Lett. 2011, 13, 3624ꢀ
3627; b) D. Łyżwa, K. Dudziński, P. Kwiatkowski, Org. Lett. 2012, 14,
1540ꢀ1543; c) P. Kwiatkowski, A. Cholewiak, A. Kasztelan, Org. Lett.
2014, 16, 5930ꢀ5933.
P. Kwiatkowski, K. Dudziński, D. Łyżwa “Non-Classical Activation of
Organocatalytic Reactions” in “Comprehensive Enantioselective
Organocatalysis: Catalysts, Reactions, and Applications” (Ed.: P.
Dalko), WileyꢀVCH, Weinheim, 2013.
[10] A. Kasztelan, M. Biedrzycki, P. Kwiatkowski, Adv. Synth. Catal. 2016,
358, 2962ꢀ2969.
Acknowledgements
[11] a) R. Dalpozzo, Chem. Soc. Rev. 2015, 44, 742ꢀ778; b) P. S. Bhadury,
J. Pang, Current Org. Chem. 2014, 18, 2108ꢀ2124; c) S.ꢀL. You, Q. Cai,
M. Zeng, Chem. Soc. Rev. 2009, 38, 2190ꢀ2201.
This work was financially supported by the Polish National
Science Centre (Sonata Bis 3, DECꢀ2013/10/E/ST5/00348).
[12] J. Nie, H.ꢀC. Guo, D. Cahard, J.ꢀA. Ma, Chem. Rev. 2011, 111, 455ꢀ
529.
Keywords: asymmetric organocatalysis • chiral Brønsted acids •
FriedelꢀCrafts reaction • highꢀpressure synthesis • trifluoromethyl
group
[13] For examples of highꢀpressure promoted enantioselective additions of
aromatic compounds to carbonyl group, see: a) P. Kwiatkowski, E.
Wojaczyńska, J. Jurczak, Tetrahedron: Asymmetry 2003, 14, 3643ꢀ
3645; b) P. Kwiatkowski, E. Wojaczyńska, J. Jurczak, J. Mol. Catal. A:
Chem. 2006, 257, 124ꢀ131; and ref. [10].
[1]
[2]
[3]
M. Rueping, D. Parmar, E. Sugiono, Eds. “Asymmetric Brønsted Acid
Catalysis” WileyꢀVCH, Weinheim, 2016.
[14] a) J. Nie, G.ꢀW. Zhang, L. Wang, A. Fu, Y. Zheng, J.ꢀA. Ma, Chem.
Commun. 2009, 2356ꢀ2358; b) J. Nie, G.ꢀW. Zhang, L. Wang, D.ꢀH.
Zheng, Y. Zheng, J.ꢀA. Ma, Eur. J. Org. Chem. 2009, 3145ꢀ3149; c) A.
Fu, W. Meng, H. Li, J. Nie, J.ꢀA. Ma, Org. Biomol. Chem. 2014, 12,
1908ꢀ1918.
T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. Int. Ed. 2004,
43, 1566ꢀ1568.
a) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356ꢀ5357;
b) D. Uraguchi, K. Sorimachi, M. Terada J. Am. Chem. Soc. 2004, 126,
11804ꢀ11805.
[15] For other reactions of indoles with carbonyl compounds and imines
catalyzed by chiral phosphoric acids, see: a) W. Kashikura, J. Itoh, K.
Mori, T. Akiyama, Chem. Asian J. 2010, 5, 470ꢀ472; b) G. B. Rowland,
E. B. Rowland, Y. Liang, J. A. Perman, J. C. Antilla, Org. Lett. 2007, 9,
2609ꢀ2611; c) M. Terada, S. Yokoyama, K. Sorimachi, D. Uraguchi,
Adv. Synth. Catal. 2007, 349, 1863ꢀ1867; d) Q. Kang, Z.ꢀA. Zhao, S.ꢀL.
You, J. Am. Chem. Soc. 2007, 129, 1484ꢀ1485; e) G.ꢀW. Zhang, L.
Wang, J. Nie, J.ꢀA. Ma, Adv. Synth. Catal. 2008, 350, 1457ꢀ1463; f) D.
Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem., Int. Ed.
2008, 47, 5661ꢀ5665; g) G.ꢀW. Zhang, L. Wang, J. Nie, J.ꢀA. Ma,. Adv.
Synth. Catal. 2008, 350, 1457ꢀ1463; h) R. Husmann, E. Sugiono, S.
Mersmann, G. Raabe, M. Rueping, C. Bolm, Org. Lett. 2011, 13, 1044ꢀ
1047; i) M. Rueping, S. Raja, A. Núñez, Adv. Synth. Catal. 2011, 353,
563ꢀ568; j) J. Feng, W. Yan, D. Wang, P. Li, Q. Sun, R. Wang, Chem.
Commun. 2012, 48, 8003ꢀ8005; k) K.ꢀF. Zhang, J. Nie, R. Guo, Y.
Zheng, J.ꢀA. Ma, Adv. Synth. Catal. 2013, 355, 3497ꢀ3502; l) X. Li, D.
Chen, H. Gu, X. Lin, Chem. Commun. 2014, 7538ꢀ7541.
[4]
a) D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114,
9047ꢀ9153; b) M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev.
2011, 40, 4539ꢀ4549; c) M. Terada, Synthesis 2010, 1929ꢀ1982; d) M.
Terada, Bull. Chem. Soc. Jpn. 2010, 83, 101ꢀ119; e) D. Kampen, C. M.
Reisinger, B. List, Top. Curr. Chem. 2010, 291, 395ꢀ456; f) A. Zamfir, S.
Schenker, M. Freund, S. B. Tsogoeva, Org. Biomol. Chem. 2010, 8,
5262ꢀ5276; g) M. Terada, Chem. Commun. 2008, 4097ꢀ4112; h) T.
Akiyama, Chem. Rev. 2007, 107, 5744ꢀ5758; i) T. Akiyama, J. Itoh, K.
Fuchibe, Adv. Synth. Catal. 2006, 348, 999ꢀ1010.
[5]
[6]
F. Giacalone, M. Gruttadauria, P. Agrigento, R. Noto Chem. Soc. Rev.
2012, 41, 2406ꢀ2447.
a) R. Van Eldik, F. G. Klaerner, Eds. High Pressure Chemistry:
Synthetic Mechanistic and Supercritical Applications, WileyꢀVCH:
Weinheim, 2002; b) K. Matsumoto, R. M. Acheson, Eds. Organic
Synthesis at High Pressure, Wiley: New York, 1991; c) J. Jurczak, B.
Baranowski, Eds. High Pressure Chemical Synthesis, Elsevier,
Amsterdam, 1989.
[16] a) S. Hoffmann, A. M. Seayad, B. List, B. Angew. Chem. Int. Ed. 2005,
44, 7424–7427; b) G. Adair, S. Mukherjee, B. List, AldrichimicaActa
2008, 41, 31–39; c) M. Klussmann, L. Ratjen, S. Hoffmann, V.
Wakchaure, R. Goddard, B. List, Synlett 2010, 2189ꢀ2192.
[7]
The highꢀpressure accelerates reactions with a negative volume of
activation: a) T. Asano, W. J. Le Noble Chem. Rev. 1978, 78, 407ꢀ489;
b) R. Van Eldik, T. Asano, W. J. Le Noble Chem. Rev. 1989, 89, 549ꢀ
688; c) A. Drljaca, C. D. Hubbard, R. Van Eldik, T. Asano, M. V.
Basilevsky, W. J. Le Noble, W. J. Chem. Rev. 1998, 98, 2167ꢀ2290; d)
G. Jenner J. Phys. Org. Chem. 2002, 15, 1ꢀ13; e) H. Wiebe, J. Spooner,
N. Boon, E. Deglint, E. Edwards, P. Dance, N. Weinberg J. Phys. Chem.
C 2012, 116, 2240ꢀ2245; f) J. Spooner, H. Wiebe, N. Boon, E. Deglint,
E. Edwards, B. Yanciw, B. Patton, L. Thiele, P. Dance, N. Weinberg
Phys. Chem. Chem. Phys. 2012, 14, 2264ꢀ2277.
[17] a) P. GarcíaꢀGarcía, F. Lay, P. GarcíaꢀGarcía, C. Rabalakos, B. List,
Angew. Chem. Int. Ed. 2009, 48, 4363ꢀ4366; b) L.ꢀY. Chen, H. He, W.ꢀ
H. Chan, A. W. M. Lee, J. Org. Chem. 2011, 76, 7141ꢀ7147; c) T.
James, M. van Gemmeren, B. List, Chem. Rev. 2015, 115, 9388ꢀ9409.
[18] For details see Supporting information.
This article is protected by copyright. All rights reserved.