IDPi Catalysis.
ACDC
Brønsted acids
Lewis acids
enantioselective catalysis
organocatalysis
silylium ions
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
09 Sep 2019
09 Sep 2019
Historique:
received:
23
01
2019
pubmed:
7
3
2019
medline:
7
3
2019
entrez:
7
3
2019
Statut:
ppublish
Résumé
High acidity and structural confinement are pivotal elements in asymmetric acid catalysis. The recently introduced imidodiphosphorimidate (IDPi) Brønsted acids have met with remarkable success in combining those features, acting as powerful Brønsted acid catalysts and "silylium" Lewis acid precatalysts in numerous thus far inaccessible transformations. Substrates as challenging to activate as simple olefins were readily transformed, ketones were employed as acceptors in aldolizations allowing sub-ppm level catalysis, whereas enolates of the smallest donor aldehyde, acetaldehyde, did not polymerize but selectively added a single time to a variety of acceptor aldehydes.
Identifiants
pubmed: 30840780
doi: 10.1002/anie.201900932
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
12761-12777Subventions
Organisme : H2020 European Research Council
ID : CHAOS
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
M. Schmeißer, P. Sartori, B. Lippsmeier, Chem. Ber. 1970, 103, 868-879;
H. W. Roesky, H. H. Giere, Z. Naturforsch. B 1970, 25, 773-776.
U. Wannagat, W. Liehr, Angew. Chem. 1957, 69, 783-784.
H. Vorbrüggen, K. Krolikiewicz, Angew. Chem. Int. Ed. Engl. 1975, 14, 421-422;
Angew. Chem. 1975, 87, 417-417.
T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett. 1980, 21, 71-74.
B. Mathieu, L. Ghosez, Tetrahedron Lett. 1997, 38, 5497-5500.
A. Ishii, O. Kotera, T. Saeki, K. Mikami, Synlett 1997, 1145-1146.
J. Foropoulos, D. D. Desmarteau, Inorg. Chem. 1984, 23, 3720-3723.
K. Ishihara, Y. Hiraiwa, H. Yamamoto, Synlett 2001, 1851-1854;
W. Gati, H. Yamamoto, Acc. Chem. Res. 2016, 49, 1757-1768.
E. M. Carreira, R. A. Singer, Tetrahedron Lett. 1994, 35, 4323-4326;
T. K. Hollis, B. Bosnich, J. Am. Chem. Soc. 1995, 117, 4570-4581.
S. Mayer, B. List, Angew. Chem. Int. Ed. 2006, 45, 4193-4195;
Angew. Chem. 2006, 118, 4299-4301.
D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
Angew. Chem. 2004, 116, 1592-1594.
P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363-4366;
Angew. Chem. 2009, 121, 4427-4430.
A manuscript including all experimental pKa values discussed in this Minireview is currently in preparation.
T. James, M. van Gemmeren, B. List, Chem. Rev. 2015, 115, 9388-9409.
I. Čorić, B. List, Nature 2012, 483, 315-319.
S. Liao, I. Čorić, Q. Wang, B. List, J. Am. Chem. Soc. 2012, 134, 10765-10768;
J. H. Kim, I. Čorić, S. Vellalath, B. List, Angew. Chem. Int. Ed. 2013, 52, 4474-4477;
Angew. Chem. 2013, 125, 4570-4573;
J. H. Kim, I. Čorić, C. Palumbo, B. List, J. Am. Chem. Soc. 2015, 137, 1778-1781;
J. H. Kim, A. Tap, L. Liu, B. List, Synlett 2017, 28, 333-336.
S. Lee, P. S. J. Kaib, B. List, J. Am. Chem. Soc. 2017, 139, 2156-2159;
S. Lee, P. S. J. Kaib, B. List, Synlett 2017, 28, 1478-1480.
L. M. Yagupolskii, V. N. Petrik, N. V. Kondratenko, L. Sooväli, I. Kaljurand, I. Leito, I. A. Koppel, J. Chem. Soc. Perkin Trans. 2 2002, 1950-1955.
S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763-2793;
M. Yus, C. Gonz, F. Foubelo, Chem. Rev. 2011, 111, 7774-7854.
T. Herold, R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1978, 17, 768-769;
Angew. Chem. 1978, 90, 822-823.
For a selection of chiral allylating agents, see: I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 14891-14899.
A. Hosomi, H. Sakurai, Tetrahedron Lett. 1976, 17, 1295-1298.
Nucleophilicity parameter N=1.68, nucleophile-specific sensitivity parameter sN=1.00 (J. Ammer, C. Nolte, H. Mayr, J. Am. Chem. Soc. 2012, 134, 13902-13911), cf. allyltri(n-butyl)tin: N=5.46, sN=0.89 (Ref. [67]).
K. Furuta, M. Mouri, H. Yamamoto, Synlett 1991, 561-562;
K. Ishihara, M. Mouri, Q. Gao, T. Maruyama, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 11490-11495.
D. R. Gauthier, Jr., E. M. Carreira, Angew. Chem. Int. Ed. Engl. 1996, 35, 2363;
Angew. Chem. 1996, 108, 2521-2365.
Methallyltrimethylsilane: N=4.41, sN=0.96 (J. Ammer, C. Nolte, H. Mayr, J. Am. Chem. Soc. 2012, 134, 13902-13911).
M. Mahlau, P. García-García, B. List, Chem. Eur. J. 2012, 18, 16283-16287.
P. S. J. Kaib, L. Schreyer, S. Lee, R. Properzi, B. List, Angew. Chem. Int. Ed. 2016, 55, 13200-13203;
Angew. Chem. 2016, 128, 13394-13397.
L. Krasnova, C.-H. Wong, Annu. Rev. Biochem. 2016, 85, 599-630;
M. M. Faul, B. E. Huff, Chem. Rev. 2000, 100, 2407-2473;
E. J. Kang, E. Lee, Chem. Rev. 2005, 105, 4348-4378.
Selected examples of previously reported addition reactions to cyclic oxocarbenium ions/ion intermediates:
M. Braun, W. Kotter, Angew. Chem. Int. Ed. 2004, 43, 514-517;
Angew. Chem. 2004, 116, 520-523;
S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198-7199;
P. N. Moquist, T. Kodama, S. E. Schaus, Angew. Chem. Int. Ed. 2010, 49, 7096-7100;
Angew. Chem. 2010, 122, 7250-7254;
P. Maity, H. D. Srinivas, M. P. Watson, J. Am. Chem. Soc. 2011, 133, 17142-17145;
Z. Yang, Y. He, F. D. Toste, J. Am. Chem. Soc. 2016, 138, 9775-9778.
S. Lee, H. Y. Bae, B. List, Angew. Chem. Int. Ed. 2018, 57, 12162-12166;
Angew. Chem. 2018, 130, 12339-12343.
D. S. Allgäuer, H. Jangra, H. Asahara, Z. Li, Q. Chen, H. Zipse, A. R. Ofial, H. Mayr, J. Am. Chem. Soc. 2017, 139, 13318-13329.
E. M. Carreira, L. Kvaerno, Classics in Stereoselective Synthesis, Wiley, Hoboken, 2009;
K. Hermann, H. Wynberg, J. Org. Chem. 1979, 44, 2238-2244;
M. Sawamura, H. Hamashima, Y. Ito, J. Am. Chem. Soc. 1992, 114, 8295-8296;
T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106;
Angew. Chem. 1996, 108, 103-105;
S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192-1194;
Y. Zhang, W. Wang, Catal. Sci. Technol. 2012, 2, 42-53;
C. Hui, F. Pu, J. Xu, Chem. Eur. J. 2017, 23, 4023-4036.
J. Y. Kang, R. G. Carter, Org. Lett. 2012, 14, 3178-3181;
B. M. Trost, K. Hirano, Org. Lett. 2012, 14, 2446-2449.
G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev. 2015, 115, 9922-9980;
D. Monge, H. Jiang, Y. Alvarez-Casao, Chem. Eur. J. 2015, 21, 4494-4504;
N. Kumagai, M. Shibasaki, Chem. Eur. J. 2016, 22, 15192-15200.
T. Gatzenmeier, M. van Gemmeren, Y. Xie, D. Höfler, M. Leutzsch, B. List, Science 2016, 351, 949-952;
D. Höfler, M. van Gemmeren, P. Wedemann, K. Kaupmees, I. Leito, M. Leutzsch, J. B. Lingnau, B. List, Angew. Chem. Int. Ed. 2017, 129, 1433-1437;
D. Höfler, R. Goddard, N. Nöthling, B. List, Synlett 2019, 30, 433-436.
T. Gatzenmeier, P. S. J. Kaib, J. B. Lingnau, R. Goddard, B. List, Angew. Chem. Int. Ed. 2018, 57, 2464-2468;
Angew. Chem. 2018, 130, 2489-2493.
R. Mahrwald, Modern Aldol Reactions, Wiley-VCH, Weinheim, 2004;
R. Mahrwald, Modern Methods in Stereoselective Aldol Reactions, Wiley-VCH, Weinheim, 2013;
M. Frías, W. Cieślik, A. Fraile, A. Rosado-Abón, A. F. Garrido-Castro, F. Yuste, J. Alemán, Chem. Eur. J. 2018, 24, 10906-10933;
S. Hosokawa, Tetrahedron Lett. 2018, 59, 77-88.
M. Hatano, E. Takagi, K. Ishihara, Org. Lett. 2007, 9, 4527-4530.
S. E. Denmark, Y. Fan, J. Am. Chem. Soc. 2002, 124, 4233-4235;
S. E. Denmark, Y. Fan, M. D. Eastgate, J. Org. Chem. 2005, 70, 5235-5248.
K. Oisaki, D. Zhao, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 7164-7165.
H. Y. Bae, D. Höfler, P. S. J. Kaib, P. Kasaplar, C. K. De, A. Döhring, S. Lee, K. Kaupmees, I. Leito, B. List, Nat. Chem. 2018, 10, 888-894.
S. E. Denmark, S. K. Ghosh, Angew. Chem. Int. Ed. 2001, 40, 4759-4762;
Angew. Chem. 2001, 113, 4895-4898.
E. J. Corey, C.-M. Yu, S. S. Kim, J. Am. Chem. Soc. 1989, 111, 5495-5496.
E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838.
T. D. Machajewski, C.-H. Wong, Angew. Chem. Int. Ed. 2000, 39, 1352;
Angew. Chem. 2000, 112, 1406-1374.
S. E. Denmark, S. K. Ghosh, Angew. Chem. Int. Ed. 2001, 40, 4759-4762;
Angew. Chem. 2001, 113, 4895-4898.
A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798-6799;
N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423;
Angew. Chem. 2004, 116, 2474-2477;
T. Kano, Y. Yamaguchi, Y. Tanaka, K. Maruoka, Angew. Chem. Int. Ed. 2007, 46, 1738-1740;
Angew. Chem. 2007, 119, 1768-1770;
M. Markert, U. Scheffler, R. Mahrwald, J. Am. Chem. Soc. 2009, 131, 16642-16643.
S. E. Denmark, T. Bui, J. Org. Chem. 2005, 70, 10190-10193;
Y. Hayashi, T. Itoh, S. Aratake, H. Ishikawa, Angew. Chem. Int. Ed. 2008, 47, 2082-2084;
Angew. Chem. 2008, 120, 2112-2114;
S. Hu, L. Zhang, J. Li, S. Luo, J.-P. Cheng, Eur. J. Org. Chem. 2011, 3347-3352.
L. Schreyer, P. S. J. Kaib, V. N. Wakchaure, C. Obradors, R. Properzi, S. Lee, B. List, Science 2018, 362, 216-219.
M. B. Boxer, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 48-49.
C. H. Cheon, H. Yamamoto, Chem. Commun. 2011, 47, 3043-3056;
D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047-9153.
K. Kaupmees, N. Tolstoluzhsky, S. Raja, M. Rueping, I. Leito, Angew. Chem. Int. Ed. 2013, 52, 11569-11572;
Angew. Chem. 2013, 125, 11783-11786.
N. Tsuji, J. L. Kennemur, T. Buyck, S. Lee, S. Prévost, P. S. J. Kaib, D. Bykov, C. Farès, B. List, Science 2018, 359, 1501-1505.
B. B. Snider, Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon Press, New York, 1991, pp. 527-561.
Selected examples:
S. R. Crosby, J. R. Harding, C. D. King, G. D. Parker, C. L. Willis, Org. Lett. 2002, 4, 577-580;
C. S. J. Barry, S. R. Crosby, J. R. Harding, R. A. Hughes, C. D. King, G. D. Parker, C. L. Willis, Org. Lett. 2003, 5, 2429-2432;
A. J. Bunt, C. D. Bailey, B. D. Cons, S. J. Edwards, J. D. Elsworth, T. Pheko, C. L. Willis, Angew. Chem. Int. Ed. 2012, 51, 3901-3904;
Angew. Chem. 2012, 124, 3967-3970;
M. J. Cloninger, L. E. Overman, J. Am. Chem. Soc. 1999, 121, 1092-1093;
R. Jasti, J. Vitale, S. C. Rychnovsky, J. Am. Chem. Soc. 2004, 126, 9904-9905.
Y. Xie, G.-J. Cheng, S. Lee, P. S. J. Kaib, W. Thiel, B. List, J. Am. Chem. Soc. 2016, 138, 14538-14541.
G. C. Tsui, L. Liu, B. List, Angew. Chem. Int. Ed. 2015, 54, 7703-7706;
Angew. Chem. 2015, 127, 7814-7818;
L. Liu, P. S. J. Kaib, A. Tap, B. List, J. Am. Chem. Soc. 2016, 138, 10822-10825;
C. Lalli, P. van de Weghe, Chem. Commun. 2014, 50, 7495-7498;
J. Liu, J. Zhou, C. Wang, D. Liang, Z. Li, Y. Zou, Q. Wang, A. Goeke, Chem. Eur. J. 2016, 22, 6258-6261.
A. C. Spivey, L. Laraia, A. R. Bayly, H. S. Rzepa, A. J. P. White, Org. Lett. 2010, 12, 900-903.
T. L. Gresham, T. R. Steadman, J. Am. Chem. Soc. 1949, 71, 737-738.
K. A. Jørgensen, Angew. Chem. Int. Ed. 2000, 39, 3558-3588;
Angew. Chem. 2000, 112, 3702-3733.
M. Bednarski, S. J. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060-7067;
J. Guin, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2012, 51, 8859-8863;
Angew. Chem. 2012, 124, 8989-8993;
L. Lin, Y. Kuang, X. Liu, X. Feng, Org. Lett. 2011, 13, 3868-3871;
Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146;
M. P. Doyle, M. Valenzuela, P. Huang, Proc. Natl. Acad. Sci. USA 2004, 101, 5391-5395.
R. B. Woodward, R. Z. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970;
L. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1977.
V. K. Aggarwal, G. P. Vennall, P. N. Davey, C. Newman, Tetrahedron Lett. 1997, 38, 2569-2572.
L. Liu, H. Kim, Y. Xie, C. Farès, P. S. J. Kaib, R. Goddard, B. List, J. Am. Chem. Soc. 2017, 139, 13656-13659.
H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77.
H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512.
M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368-3398;
Angew. Chem. 2004, 116, 3448-3479;
V. Rodriguez-Ruiz, R. Carlino, S. Bezzenine-Lafollée, R. Gil, D. Prim, E. Schulz, J. Hannedouche, Dalton Trans. 2015, 44, 12029-12059.
Y. Nishiyama, T. Wada, S. Asaoka, T. Mori, T. A. McCarty, N. D. Kraut, F. V. Bright, Y. Inoue, J. Am. Chem. Soc. 2008, 130, 7526-7527;
C. S. Sevov, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 9303-9306;
J. Schlüter, M. Blazejak, F. Boeck, L. Hintermann, Angew. Chem. Int. Ed. 2015, 54, 4014-4017;
Angew. Chem. 2015, 127, 4086-4089;
H. Murayama, K. Nagao, H. Ohmiya, M. Sawamura, Org. Lett. 2015, 17, 2039-2041;
H. Shigehisa, M. Hayashi, H. Ohkawa, T. Suzuki, H. Okayasu, M. Mukai, A. Yamazaki, R. Kawai, H. Kikuchi, Y. Satoh, A. Fukuyama, K. Hiroya, J. Am. Chem. Soc. 2016, 138, 10597-10604;
Z. Yang, H. Li, S. Li, M.-T. Zhang, S. Luo, Org. Chem. Front. 2017, 4, 1037-1041.
M. E. Jung, G. Piizzi, Chem. Rev. 2005, 105, 1735-1766.
K. U. Wendt, K. Poralla, G. E. Schulz, Science 1997, 277, 1811-1815.
S.-S. Gao, M. Garcia-Borràs, J. S. Barber, Y. Hai, A. Duan, N. K. Garg, K. N. Houk, Y. Tang, J. Am. Chem. Soc. 2017, 139, 3639-3642.
B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396;
S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475-2479.
Figure 7 c was taken from the following publication with permission from Elsevier (license number 4504111108016): C. Liu, M. Yuan, X. Xu, L. Wang, A. T. Keatinge-Clay, Z. Deng, S. Lin, J. Zheng, J. Struct. Biol. 2018, 203, 135-141.