Stronger Brønsted Acids: Recent Progress

Chemical Reviews

Volumn 115, Issue 17, 2015, Pages 9277-9306

  Akiyama, Takahiko ^a   Mori, Keiji ^a,b  

^a GAKUSHUIN UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS;

CARBON-CARBON BOND FORMATION REACTIONS; DICARBOXYLIC ACID; DISULFONIC ACID; EFFICIENT CATALYSTS; RECENT PROGRESS; SYNTHETIC UTILITY; TRIFLUOROMETHANE SULFONIC ACID;

CATALYSTS;

EID: 84941046960     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/acs.chemrev.5b00041     Document Type: Review

References (246)

1. Schinzer, D. Selectivities in Lewis Acid Promoted Reactions; Kluwer Academic: Dordrecht, 1989.
2. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000.
3. In Acid Catalysis in Modern Organic Synthesis; Yamamoto, H., Ishihara, K., Eds.; Wiley-VCH: Weinheim, 2008; Vols. 1 and 2.
4. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W. L. Rare-Earth Metal Triflates in Organic Synthesis Chem. Rev. 2002, 102, 2227-2302 10.1021/cr010289i
5. For examples, see: Mukaiyama, T.; Kobayashi, S. Org. React. (N.Y.) 1994, 46, 1-103 10.1002/0471264180.or046.01
6. Johnson, J. S.; Evans, D. A. Chiral Bis(oxazoline) Copper(II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene Reactions Acc. Chem. Res. 2000, 33, 325-335 10.1021/ar960062n
7. Shibasaki, M.; Kanai, M.; Funabashi, K. Recent Progress in Asymmetric Two-Center Catalysis Chem. Commun. 2002, 1989-1999 10.1039/b203495f
8. Yamamoto, H.; Ishihara, K. In Acid Catalysis in Modern Organic Synthesis; Yamamoto, H.; Ishihara,. K., Ed.; Wiley-VCH: Weinheim, 2008; p 35-62.
9. Haszeldine, R. N.; Kidd, J. M. Perfluoroalkyl Derivatives of Sulphur. Part I. Trifluoromethanesulphonic Acid J. Chem. Soc. 1954, 4228-4232 10.1039/jr9540004228
10. 2NH Inorg. Chem. 1984, 23, 3720-3723 10.1021/ic00191a011
11. Bordwell, F. G. Equilibrium Acidities in Dimethyl Sulfoxide Solution Acc. Chem. Res. 1988, 21, 456-463 10.1021/ar00156a004
12. Akiyama, T.; Itoh, J.; Fuchibe, K. Recent Progress in Chiral Brønsted Acid Catalysis Adv. Synth. Catal. 2006, 348, 999-1010 10.1002/adsc.200606074
13. Akiyama, T. Stronger Brønsted Acids Chem. Rev. 2007, 107, 5744-5758 10.1021/cr068374j
14. Akiyama, T. In Acid Catalysis in Modern Organic Synthesis; Yamamoto, H.; Ishihara, K., Ed.; Wiley-VCH: Weinheim, 2008; pp 62-107.
15. Hashimoto, T. In Asymmetric Organocatalysis 2: Brønsted Acid Catalysts Other than Phosphoric Acids; Maruoka, K., Ed.; Georg Thieme Verlag: Stuttgart, New York, 2012; Vol. 2, pp 279-296.
16. Ishihara, K.; Kaneeda, M.; Yamamoto, H. Lewis Acid Assisted Chiral Brønsted Acid for Enantioselective Protonation of Silyl Enol Ethers and Ketene Bis(trialkylsilyl) Acetals J. Am. Chem. Soc. 1994, 116, 11179-11180 10.1021/ja00103a052
17. Nakamura, S.; Ishihara, K.; Yamamoto, H. Enantioselective Biomimetic Cyclization of Isoprenoids Using Lewis Acid-Assisted Chiral Brønsted Acids: Abnormal Claisen Rearrangements and Successive Cyclizations J. Am. Chem. Soc. 2000, 122, 8131-8140 10.1021/ja001165a
18. For a review on Lewis-acid-assisted Brønsted acid, see: Yamamoto, H.; Futatsugi, K. Designer Acids: Combined Acid Catalysis for Asymmetric Synthesis Angew. Chem., Int. Ed. 2005, 44, 1924-1942 10.1002/anie.200460394
19. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Brønsted Acid Angew. Chem., Int. Ed. 2004, 43, 1566-1568 10.1002/anie.200353240
20. Uraguchi, D.; Terada, M. Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation J. Am. Chem. Soc. 2004, 126, 5356-5357 10.1021/ja0491533
21. Connon, S. J. Chiral Phosphoric Acids: Powerful Organocatalysts for Asymmetric Addition Reactions to Imines Angew. Chem., Int. Ed. 2006, 45, 3909-3912 10.1002/anie.200600529
22. Terada, M. Binaphthol-Derived Phosphoric Acid as a Versatile Catalyst for Enantioselective Carbon-Carbon Bond Forming Reactions Chem. Commun. 2008, 4097-4112 10.1039/b807577h
23. Terada, M. Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations Synthesis 2010, 2010, 1929-1982 10.1055/s-0029-1218801
24. Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S. M. Chiral BINOL-Derived Phosphoric Acids: Privileged Brønsted Acid Organocatalysts for C-C Bond Formation Reactions Org. Biomol. Chem. 2010, 8, 5262 10.1039/c0ob00209g
25. Terada, M. Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Carbon-Carbon Bond Forming Reactions Bull. Chem. Soc. Jpn. 2010, 83, 101-119 10.1246/bcsj.20090268
26. Terada, M. Enantioselective Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Phosphoric Acid Catalysts Curr. Org. Chem. 2011, 15, 2227-2256 10.2174/138527211796150732
27. Rueping, M.; Kuenkel, A.; Atodiresei, I. Chiral Brønsted Acids in Enantioselective Carbonyl Activations-Activation Modes and Applications Chem. Soc. Rev. 2011, 40, 4539-4549 10.1039/c1cs15087a
28. Akiyama, T. In Asymmetric Organocatalysis 2: Brønsted Base and Acid Catalysts, and Additional Topics; Maruoka, K., Ed.; Georg Thieme Verlag: Stuttgart, New York, 2012; Vol. 2, pp 169-217.
29. Terada, M.; Momiyama, N. In Asymmetric Organocatalysis 2: Brønsted Base and Acid Catalysts, and Additional Topics; Maruoka, K., Ed.; Georg Thieme Verlag: Stuttgart, New York, 2012; Vol. 2, pp 219-278.
30. Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates Chem. Rev. 2014, 114, 9047-9153 10.1021/cr5001496
31. Sigman, M. S.; Jacobsen, E. N. Schiff Base Catalysts for the Asymmetric Strecker Reaction Identified and Optimized from Parallel Synthetic Libraries J. Am. Chem. Soc. 1998, 120, 4901-4902 10.1021/ja980139y
32. Sigman, M. S.; Vachal, P.; Jacobsen, E. N. A General Catalyst for the Asymmetric Strecker Reaction Angew. Chem., Int. Ed. 2000, 39, 1279-1281 10.1002/(SICI)1521-3773(20000403)39:71279::AID-ANIE12793.0.CO;2-U
33. Okino, T.; Hoashi, Y.; Takemoto, Y. Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts J. Am. Chem. Soc. 2003, 125, 12672-12673 10.1021/ja036972z
34. Miyabe, H.; Takemoto, Y. Discovery and Application of Asymmetric Reaction by Multi-Functional Thioureas Bull. Chem. Soc. Jpn. 2008, 81, 785-795 10.1246/bcsj.81.785
35. Takemoto, Y. Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions Chem. Pharm. Bull. 2010, 58, 593-601 10.1248/cpb.58.593
36. Huang, Y.; Rawal, V. H. Hydrogen-Bond-Promoted Hetero-Diels-Alder Reactions of Unactivated Ketones J. Am. Chem. Soc. 2002, 124, 9662-9663 10.1021/ja0267627
37. Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Hydrogen Bonding: Single Enantiomers from a Chiral-Diol Catalyst Nature 2003, 424, 146 10.1038/424146a
38. Storer, R. I.; Aciro, C.; Jones, L. H. Squaramides: Physical Properties, Synthesis and Applications Chem. Soc. Rev. 2011, 40, 2330-2346 10.1039/c0cs00200c
39. Schreiner, P. R. Metal-Free Organocatalysis through Explicit Hydrogen Bonding Interactions Chem. Soc. Rev. 2003, 32, 289-296 10.1039/b107298f
40. Yu, X.; Wang, W. Hydrogen-Bond-Mediated Asymmetric Catalysis Chem.-Asian J. 2008, 3, 516-532 10.1002/asia.200700415
41. Doyle, A. G.; Jacobsen, E. N. Small-Molecule H-Bond Donors in Asymmetric Catalysis Chem. Rev. 2007, 107, 5713-5743 10.1021/cr068373r
42. In Hydrogen Bonding in Organic Synthesis, Pihko, P., Ed.; Wiley-VCH: Weinheim, 2009.
43. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Asymmetric Cooperative Catalysis of Strong Brønsted Acid-Promoted Reactions Using Chiral Ureas Science 2010, 327, 986-990 10.1126/science.1182826
44. Akiyama, T. In Hydrogen Bonding in Organic Synthesis; Pihko, P., Ed.; Wiley-VCH: Weinheim, 2009; pp 5-14.
45. a Values of Chiral Brønsted Acid Catalysts: Phosphoric Acids/Amides, Sulfonyl/Sulfuryl Imides, and Perfluorinated TADDOLs (TEFDDOLs) Chem.-Eur. J. 2011, 17, 8524-8528 10.1002/chem.201101157
46. Kaupmees, K.; Tolstoluzhsky, N.; Raja, S.; Rueping, M.; Leito, I. On the Acidity and Reactivity of Highly Effective Chiral Brønsted Acid Catalysts: Establishment of an Acidity Scale Angew. Chem., Int. Ed. 2013, 52, 11569-11572 10.1002/anie.201303605
47. Mofaddela, N.; Krajiana, H.; Villeminb, D.; Desbènea, P. L. Enantioseparation of binaphthol and its monoderivatives by cyclodextrin-modified capillary zone electrophoresis: A mathematical approach Talanta 2009, 78, 631-637 10.1016/j.talanta.2008.12.027
48. Li, X.; Deng, H.; Zhang, B.; Li, J.; Zhang, L.; Luo, S.; Cheng, J.-P. Physical Organic Study of Structure-Activity-Enantioselectivity Relationships in Asymmetric Bifunctional Thiourea Catalysis: Hints for the Design of New Organocatalysts Chem.-Eur. J. 2010, 16, 450-455 10.1002/chem.200902430
49. Yang, C.; Xue, X.-S.; Jin, J.-L.; Li, X.; Cheng, J.-P. Theoretical Study on the Acidities of Chiral Phosphoric Acids in Dimethyl Sulfoxide: Hints for Organocatalysis J. Org. Chem. 2013, 78, 7076-7085 10.1021/jo400915f
50. Ni, X.; Li, X.; Wang, Z.; Cheng, J.-P. Squaramide Equilibrium Acidities in DMSO Org. Lett. 2014, 16, 1786-1789 10.1021/ol5005017
51. Yang, C.; Xue, X.-S.; Li, X.; Cheng, J.-P. Computational Study on the Acidic Constants of Chiral Brønsted Acids in Dimethyl Sulfoxide J. Org. Chem. 2014, 79, 4340-4351 10.1021/jo500158e
52. Beutner, G. L.; Denmark, S. E. Lewis Base Catalysis of the Mukaiyama Directed Aldol Reaction: 40 Years of Inspiration and Advances Angew. Chem., Int. Ed. 2013, 52, 9086-9096 10.1002/anie.201302084
53. Kan, S. B. J.; Ng, K. K.-H.; Paterson, I. The Impact of the Mukaiyama Aldol Reaction in Total Synthesis Angew. Chem., Int. Ed. 2013, 52, 9097-9108 10.1002/anie.201303914
54. Matsuo, J.-i.; Murakami, M. The Mukaiyama Aldol Reaction: 40 Years of Continuous Development Angew. Chem., Int. Ed. 2013, 52, 9109-9118 10.1002/anie.201303192
55. Boxer, M. B.; Yamamoto, H. Tris(trimethylsilyl)silyl-Governed Aldehyde Cross-Aldol Cascade Reaction J. Am. Chem. Soc. 2006, 128, 48-49 10.1021/ja054725k
56. For the development of TTMSS group, sees: Boxer, M. B.; Yamamoto, H. Remarkable Tris(trimethylsilyl)silyl Group for Diastereoselective [2 + 2] Cyclizations Org. Lett. 2005, 7, 3127-3129 10.1021/ol0512334
57. For a review on super Brønsted acid, see: Cheon, C. H.; Yamamoto, H. Super Brønsted acid catalysis Chem. Commun. 2011, 47, 3043-3056 10.1039/c0cc04867d
58. Boxer, M. B.; Yamamoto, H. Super Silyl Group for Diastereoselective Sequential Reactions: Access to Complex Chiral Architecture in One Pot J. Am. Chem. Soc. 2007, 129, 2762-2763 10.1021/ja0693542
59. Boxer, M. B.; Akakura, M.; Yamamoto, H. Ketone Super Silyl Enol Ethers in Sequential Reactions: Diastereoselective Generation of Tertiary Carbinols in One Pot J. Am. Chem. Soc. 2008, 130, 1580-1582 10.1021/ja7102586
60. Yamaoka, Y.; Yamamoto, H. Super Silyl Stereo-Directing Groups for Complete 1,5-Syn and -Anti Stereoselectivities in the Aldol Reactions of β-Siloxy Methyl Ketones with Aldehydes J. Am. Chem. Soc. 2010, 132, 5354-5356 10.1021/ja101076q
61. Han, Y.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. An Efficient Synthesis of 3-(Indol-3-yl)quinoxalin-2-ones with TfOH-Catalyzed Friedel-Crafts Type Coupling Reaction in Air Tetrahedron Lett. 2010, 51, 2023-2028 10.1016/j.tetlet.2010.02.031
62. Wang, F.-F.; Luo, C.-P.; Wang, Y.; Deng, G.; Yang, L. Brønsted Acid Promoted Benzylic C-H Bond Functionalization of Azaarenes: Nucleophilic Addition to Aldehydes Org. Biomol. Chem. 2012, 10, 8605-8608 10.1039/c2ob26604k
63. Galliford, C. V.; Scheidt, K. A. Pyrrolidinyl-Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic Agents Angew. Chem., Int. Ed. 2007, 46, 8748-8758 10.1002/anie.200701342
64. Zhou, F.; Liu, Y.-L.; Zhou, J. Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position Adv. Synth. Catal. 2010, 352, 1381-1407 10.1002/adsc.201000161
65. 3 C-H Functionalization Org. Lett. 2012, 14, 676-679 10.1021/ol2030982
66. Lee-Ruff, E.; Mladenova, G. Enantiomerically Pure Cyclobutane Derivatives and Their Use in Organic Synthesis Chem. Rev. 2003, 103, 1449-1483 10.1021/cr010013a
67. Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Cyclobutanes in Catalysis Angew. Chem., Int. Ed. 2011, 50, 7740-7752 10.1002/anie.201101053
68. Inanaga, K.; Takasu, K.; Ihara, M. A Practical Catalytic Method for Preparing Highly Substituted Cyclobutanes and Cyclobutenes J. Am. Chem. Soc. 2005, 127, 3668-3669 10.1021/ja042661s
69. 2NH-catalyzed reactions, see: Takasu, K. Triflic Imide Catalyzed Cycloaddition Reactions Synlett 2009, 2009, 1905-1914 10.1055/s-0029-1217522
70. 2-Induced Carbon-Carbon Bond-Forming Reactions of Silyl Nucleophiles with Carbonyl Compounds: The Importance of Addition Order and Solvent Effects Synlett 2001, 2001, 1851-1854 10.1055/s-2001-18761
71. Azuma, T.; Takemoto, Y.; Takasu, K. Formal (3 + 3) Cycloaddition of Silyl Enol Ethers Catalyzed by Triflic Imide: Domino Michael Addition-Claisen Condensation Accompanied with Isomerization of Silyl Enol Ethers Chem. Pharm. Bull. 2011, 59, 1190-1193 10.1248/cpb.59.1190
72. Takasu, K.; Hosokawa, N.; Inanaga, K.; Ihara, M. Cyclobutane Ring Formation by Triflic Imide Catalyzed [2 + 2]-Cycloaddition of Allylsilanes Tetrahedron Lett. 2006, 47, 6053-6056 10.1016/j.tetlet.2006.06.102
73. Hosomi, A. Characteristics in the Reactions of Allylsilanes and Their Applications to Versatile Synthetic Equivalents Acc. Chem. Res. 1988, 21, 200-206 10.1021/ar00149a004
74. Masse, C. E.; Panek, J. S. Diastereoselective Reactions of Chiral Allyl and Allenyl Silanes with Activated C=X π-Bonds Chem. Rev. 1995, 95, 1293-1316 10.1021/cr00037a008
75. Knölker, H.-J. Stereoselective Construction of Ring Systems by Cycloaddition Reactions of Ally1triisopropylsilan J. Prakt. Chem./Chem.-Ztg. 1997, 339, 304-314 10.1002/prac.19973390158
76. Takasu, K.; Nagao, S.; Ihara, M. Construction of Highly-Functionalized Cyclopentanes from Silyl Enol Ethers and Activated Cyclopropanes by [3 + 2] Cycloaddition Catalyzed by Triflic Imide Adv. Synth. Catal. 2006, 348, 2376-2380 10.1002/adsc.200600308
77. Takasu, K.; Tanaka, T.; Azuma, T.; Takemoto, Y. Auto-Tandem Catalysis: Facile Synthesis of Substituted Alkylidenecyclohexanones by Domino (4 + 2) Cycloaddition-Elimination Reaction Chem. Commun. 2010, 46, 8246-8248 10.1039/c0cc03336g
78. Shindoh, N.; Tokuyama, H.; Takemoto, Y.; Takasu, K. Auto-Tandem Catalysis in the Synthesis of Substituted Quinolines from Aldimines and Electron-Rich Olefins: Cascade Povarov-Hydrogen-Transfer Reaction J. Org. Chem. 2008, 73, 7451-7456 10.1021/jo8009243
79. Shindoh, N.; Tokuyama, H.; Takemoto, Y.; Takasu, K. Triflic Imide Catalyzed [3 + 2] Cycloaddition of Aldimines with α,α-Dimethylallylsilane Heterocycles 2009, 77, 187-192 10.3987/COM-08-S(F)17
80. Takasu, K.; Shindoh, N.; Tokuyama, H.; Ihara, M. Catalytic Imino Diels-Alder Reaction by Triflic Imide and Its Application to One-Pot Synthesis from Three Components Tetrahedron 2006, 62, 11900-11907 10.1016/j.tet.2006.09.092
81. Akiyama, T.; Takaya, J.; Kagoshima, H. Brønsted Acid-Catalyzed Aza Diels-Alder Reaction of Danishefskys Diene with Aldimine Generated in Situ from Aldehyde and Amine in Aqueous Media Tetrahedron Lett. 1999, 40, 7831-7834 10.1016/S0040-4039(99)01630-5
82. Shindoh, N.; Kitaura, K.; Takemoto, Y.; Takasu, K. Catalyst-Controlled Torquoselectivity Switch in the 4π Ring-Opening Reaction of 2-Amino-2-azetines Giving β-Substituted α,β-Unsaturated Amidines J. Am. Chem. Soc. 2011, 133, 8470-8473 10.1021/ja202576e
83. Jung, M. E.; Chu, H. V. Preparation of a Functionalized Tetracyclic Intermediate for the Synthesis of Rhodexin A Org. Lett. 2008, 10, 3647-3649 10.1021/ol801426z
84. Shimada, N.; Stewart, C.; Tius, M. A. Asymmetric Nazarov cyclizations Tetrahedron 2011, 67, 5851-5870 10.1016/j.tet.2011.05.062
85. Audran, G.; Brémond, P.; Feuerstein, M.; Marque, S. R. A.; Santelli, M. Nazarov Reagents and Their Use in Organic Synthesis Tetrahedron 2013, 69, 8325-8348 10.1016/j.tet.2013.06.065
86. Bachu, P.; Akiyama, T. Brønsted Acid-Catalyzed Nazarov Cyclization of Pyrrole Derivatives Accelerated by Microwave Irradiation Bioorg. Med. Chem. Lett. 2009, 19, 3764-3766 10.1016/j.bmcl.2009.04.109
87. Li, W.; Shi, M. A Catalytic Method for the Preparation of Polysubstituted Cyclopentanes: [3 + 2] Cycloaddition of Vinylidenecyclopropanes with Activated Olefins Catalyzed by Triflic Imide J. Org. Chem. 2009, 74, 856-860 10.1021/jo802294s
88. Zhang, Z.; Wang, D.; Wei, Y.; Shi, M. Facile Synthesis of 2-Pyrazolines and α,β-Diamino Ketones via Regioselective Ring-Opening of Hydrazone-Tethered Aziridines Chem. Commun. 2012, 48, 9607-9609 10.1039/c2cc35135h
89. Mundal, D. A.; Avetta, C. T., Jr; Thomson, R. J. Triflimide-Catalysed Sigmatropic Rearrangement of N-Allylhydrazones as An Example of a Traceless Bond Construction Nat. Chem. 2010, 2, 294-297 10.1038/nchem.576
90. Yu, M.; Pantos, G. D.; Sessler, J. L.; Pagenkopf, B. L. Synthesis of 2,2-Bipyrroles and 2,2-Thienylpyrroles from Donor-Acceptor Cyclopropanes and 2-Cyanoheteroles Org. Lett. 2004, 6, 1057-1059 10.1021/ol049857h
91. 4-Promoted [3 + 2] Cycloaddition between Activated Donor-Acceptor Cyclopropanes and Nitriles Org. Lett. 2011, 13, 6002-6005 10.1021/ol2024423
92. Cui, B.; Ren, J.; Wang, Z. TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles J. Org. Chem. 2014, 79, 790-796 10.1021/jo402383a
93. Song, Z.; Zhao, Y.-M.; Zhai, H. One-Step Construction of Tetrahydro-5H-indolo[3,2-c]quinolines from Benzyl Azides and Indoles via a Cascade Reaction Sequence Org. Lett. 2011, 13, 6331-6333 10.1021/ol202656u
94. Yamamoto, Y. From φ- to π-Electrophilic Lewis Acids. Application to Selective Organic Transformations J. Org. Chem. 2007, 72, 7817-7831 10.1021/jo070579k
95. Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Brønsted Acid-Catalyzed Highly Stereoselective Arene-Ynamide Cyclizations. A Novel Keteniminium Pictet-Spengler Cyclization in Total Syntheses of (±)-Desbromoarborescidines A and C Org. Lett. 2005, 7, 1047-1050 10.1021/ol0473391
96. Zhang, L.; Kozmin, S. A. Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes J. Am. Chem. Soc. 2004, 126, 10204-10205 10.1021/ja046586x
97. Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. Directed Electrophilic Cyclizations: Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics J. Am. Chem. Soc. 1997, 119, 4578-4593 10.1021/ja9642673
98. 3-Hybridized C-H Bond Activation J. Am. Chem. Soc. 2010, 132, 5590-5591 10.1021/ja101633x
99. Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Alkyne Activation with Brønsted Acids, Iodine, or Gold Complexes, and Its Fate Leading to Synthetic Application Chem. Commun. 2009, 5075-5087 10.1039/b909978f
100. Jin, T.; Yang, F.; Liu, C.; Yamamoto, Y. TfOH-Catalyzed Intramolecular Alkyne-Ketone Metathesis Leading to Highly Substituted Five-Membered Cyclic Enones Chem. Commun. 2009, 3533-3535 10.1039/b905954g
101. Jin, T.; Yamamoto, Y. Gold-Catalyzed Intramolecular Carbocyclization of Alkynyl Ketones Leading to Highly Substituted Cyclic Enones Org. Lett. 2007, 9, 5259-5262 10.1021/ol702455v
102. Jin, T.; Yamamoto, Y. Gold-Catalyzed Synthesis of Polycyclic Enones from Carbon Tethered 1,3-Enynyl Carbonyls via Tandem Heteroenyne Metathesis and Nazarov Reaction Org. Lett. 2008, 10, 3137-3139 10.1021/ol801265s
103. Jin, T.; Uchiyama, J.; Himuro, M.; Yamamoto, Y. Triflic Acid-Catalyzed Cascade Cyclization of Arenyl Enynes via Acetylene-Cation Cyclization and Friedel-Crafts Type Reaction Tetrahedron Lett. 2011, 52, 2069-2071 10.1016/j.tetlet.2010.10.094
104. Hashmi, A. S. K.; Schwarz, L.; Rubenbauer, P.; Blanco, M. C. The Condensation of Carbonyl Compounds with Electron-Rich Arenes: Mercury, Thallium, Gold or a Proton? Adv. Synth. Catal. 2006, 348, 705-706 10.1002/adsc.200505464
105. Hashmi, A. S. K. Homogeneous Gold Catalysis: The Role of Protons Catal. Today 2007, 122, 211 10.1016/j.cattod.2006.10.006
106. Krater, C. M.; Hashmi, A. S. K.; Perpointner, M. A New Insight into Gold(I)-Catalyzed Hydration of Alkynes: Proton Transfer ChemCatChem 2010, 2, 1226-1230 10.1002/cctc.201000136
107. Wang, H.; Liu, L.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. An Efficient Synthesis of 4-Alkyl-2(1H)-quinazolinones and 4-Alkyl-2-chloroquinazolines from 1-(2-Alkynylphenyl)ureas Tetrahedron Lett. 2009, 50, 6841-6843 10.1016/j.tetlet.2009.09.130
108. Ye, S.; Yu, Z.-X. TfOH-Catalyzed Tandem Cyclopropane Ring Enlargement/C-C Formation/Etherification of Alkynylcyclopropanes and 1,3-Diketones to Cyclobutane-Fused Dihydrofurans Chem. Commun. 2011, 47, 794-796 10.1039/C0CC04283H
109. Yamaoka, Y.; Yoshida, T.; Shinozaki, M.; Yamada, K.-i.; Takasu, K. Development of a Brønsted Acid-Promoted Arene-Ynamide Cyclization toward the Total Syntheses of Marinoquinolines A and C and Aplidiopsamine A J. Org. Chem. 2015, 80, 957-964 10.1021/jo502467m
110. Ho, H. E.; Asao, N.; Yamamoto, Y.; Jin, T. Carboxylic Acid-Catalyzed Highly Efficient and Selective Hydroboration of Alkynes with Pinacolborane Org. Lett. 2014, 16, 4670-4673 10.1021/ol502285s
111. Sanz, R.; Miguel, D.; Martinez, A.; Alvarez-Gutierrez, J. M.; Rodriguez, E. Brønsted Acid-Catalyzed Benzylation of 1,3-Dicarbonyl Derivatives Org. Lett. 2007, 9, 2027-2030 10.1021/ol070624a
112. Jin, T.; Himuro, M.; Yamamoto, Y. Triflic Acid Catalyzed Synthesis of Spirocycles via Acetylene Cations Angew. Chem., Int. Ed. 2009, 48, 5893-5896 10.1002/anie.200901771
113. 2O and TfOH as Catalysts for Allylic Amination Reaction: A Comparative Study Eur. J. Org. Chem. 2012, 2012, 2929-2934 10.1002/ejoc.201101844
114. 3/TfOH Cocatalyzed Coupling Reaction of Terminal Alkynes with Benzylic Alcohols Chem. Commun. 2009, 45, 6487-6489 10.1039/b911905a
115. Mothe, S. R.; Kothandaraman, P.; Rao, W.; Chan, P. W. H. Rapid Access to Halohydrofurans via Brønsted Acid-Catalyzed Hydroxylation/Halocyclization of Cyclopropyl Methanols with Water and Electrophilic Halides J. Org. Chem. 2011, 76, 2521-2531 10.1021/jo102374z
116. Mothe, S. R.; Lauw, S. J. L.; Kothandaraman, P.; Chan, P. W. H. Brønsted Acid-Catalyzed Cycloisomerization of But-2-yne-1,4-diols with or without 1,3-Dicarbonyl Compounds to Tri- and Tetrasubstituted Furans J. Org. Chem. 2012, 77, 6937-6947 10.1021/jo301093f
117. Li, G.; Zhou, S.; Su, G.; Liu, Y.; Wang, P. G. Improved Synthesis of Aryl-Substituted Anthracenes and Heteroacenes J. Org. Chem. 2007, 72, 9830-9833 10.1021/jo7017334
118. Lyons, T. W.; Sanford, M. S. Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions Chem. Rev. 2010, 110, 1147-1169 10.1021/cr900184e
119. Davies, H. M. L.; Morton, D. Guiding Principles for Site Selective and Stereoselective Intermolecular C-H Functionalization by Donor/Acceptor Rhodium Carbenes Chem. Soc. Rev. 2011, 40, 1857-1869 10.1039/c0cs00217h
120. Gutekunst, W. R.; Baran, P. S. C-H Functionalization Logic in Total Synthesis Chem. Soc. Rev. 2011, 40, 1976-1991 10.1039/c0cs00182a
121. Neufeldt, S. R.; Sanford, M. S. Controlling Site Selectivity in Palladium-Catalyzed C-H Bond Functionalization Acc. Chem. Res. 2012, 45, 936-946 10.1021/ar300014f
122. Haibach, M. C.; Seidel, D. C-H Bond Functionalization through Intramolecular Hydride Transfer Angew. Chem., Int. Ed. 2014, 53, 5010-5036 10.1002/anie.201306489
123. Peng, B.; Maulide, N. The Redox-Neutral Approach to C-H Functionalization Chem.-Eur. J. 2013, 19, 13274-13287 10.1002/chem.201301522
124. Pan, S. C. Organocatalytic C-H Activation Reactions Beilstein J. Org. Chem. 2012, 8, 1374-1384 10.3762/bjoc.8.159
125. Mátyus, P.; éliás, O.; Tapolcsányi, P.; Polonka-Bálint, á.; Halász-Dajka, B. Ring-Closure Reactions of ortho-Vinyl-tert-anilines and (Di)Aza-Heterocyclic Analogues via the tert-Amino Effect: Recent Developments Synthesis 2006, 2006, 2625-2639 10.1055/s-2006-942490
126. Jurberg, I. D.; Peng, B.; Wöstefeld, E.; Wasserloos, M.; Maulide, N. Intramolecular Redox-Triggered CH Functionalization Angew. Chem., Int. Ed. 2012, 51, 1950-1953 10.1002/anie.201108639
127. 3)H Bonds Adv. Synth. Catal. 2014, 356, 1137-1171 10.1002/adsc.201301153
128. Che, X.; Zheng, L.; Dang, Q.; Bai, X. Synthesis of 7,8,9-Trisubstituted Dihydropurine Derivatives via a tert-Amino Effect Cyclization Synlett 2008, 2008, 2373-2375 10.1055/s-2008-1078212
129. Zhang, C.; Murarka, S.; Seidel, D. Facile Formation of Cyclic Aminals through a Brønsted Acid-Promoted Redox Process J. Org. Chem. 2009, 74, 419-422 10.1021/jo802325x
130. Mori, K.; Ohshima, Y.; Ehara, K.; Akiyama, T. Expeditious Construction of Quinazolines via Brønsted Acid-induced C-H Activation: Further Extension of tert-Amino Effect Chem. Lett. 2009, 38, 524-252 10.1246/cl.2009.524
131. 3)-Hydrogen by Means of Chiral Phosphoric Acid: Asymmetric Synthesis of Tetrahydroquinoline Derivatives J. Am. Chem. Soc. 2011, 133, 6166-6169 10.1021/ja2014955
132. 3 C-H Functionalization via a Chiral Brønsted Acid-Catalyzed Redox Reaction for the Synthesis of Cyclic Aminals Tetrahedron Lett. 2011, 52, 7064-7066 10.1016/j.tetlet.2011.10.062
133. Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. Catalytic Enantioselective Intramolecular Redox Reactions: Ring-Fused Tetrahydroquinolines J. Am. Chem. Soc. 2009, 131, 13226-13227 10.1021/ja905213f
134. Cao, W.; Liu, X.; Wang, W.; Lin, L.; Feng, X. Highly Enantioselective Synthesis of Tetrahydroquinolines via Cobalt(II)-Catalyzed Tandem 1,5-Hydride Transfer/Cyclization Org. Lett. 2011, 13, 600-603 10.1021/ol1028282
135. 3)-H Bond Functionalization: Intramolecular Benzylic [1,5]-Hydride Shift Tetrahedron Lett. 2014, 55, 2859-2864 10.1016/j.tetlet.2014.03.089
136. 3 C-H Bonds through a Redox-Neutral Domino Reaction Chem.-Eur. J. 2011, 17, 3101-3104 10.1002/chem.201100019
137. Kang, Y. K.; Kim, S. M.; Kim, D. Y. Enantioselective Organocatalytic C-H Bond Functionalization via Tandem 1,5-Hydride Transfer/Ring Closure: Asymmetric Synthesis of Tetrahydroquinolines J. Am. Chem. Soc. 2010, 132, 11847-11848 10.1021/ja103786c
138. sp3-H Functionalization of Ethers: A Highly Efficient Approach to Chiral Spiroethers Angew. Chem., Int. Ed. 2012, 51, 8811-8815 10.1002/anie.201204274
139. Suh, C. W.; Woo, S. B.; Kim, D. Y. Asymmetric Synthesis of Tetrahydroquinolines via Saegusa-type Oxidative Enamine Catalysis/1,5-Hydride Transfer/Cyclization Sequences Asian J. Org. Chem. 2014, 3, 399-402 10.1002/ajoc.201400022
140. Kang, Y. K.; Kim, D. Y. Enantioselective Organocatalytic Oxidative Enamine Catalysis-1,5-Hydride Transfer-Cyclization Sequences: Asymmetric Synthesis of Tetrahydroquinolines Chem. Commun. 2014, 50, 222-224 10.1039/C3CC46710D
141. sp3-H Activation and Stereoselectivity Chem.-Asian J. 2012, 7, 2569-2576 10.1002/asia.201200674
142. Chen, L.; Zhang, L.; Lv, J.; Cheng, J.-P.; Luo, S. Catalytic Enantioselective tert-Aminocyclization by Asymmetric Binary Acid Catalysis (ABC): Stereospecific 1,5-Hydrogen Transfer Chem.-Eur. J. 2012, 18, 8891-8895 10.1002/chem.201201532
143. Yu, J.; Li, Nan; Chen, D.-F.; Luo, S.-W. Cascade Hydroamination/Redox Reaction for the Synthesis of Cyclic Aminals Catalyzed by a Combined Gold Complex and Brønsted Acid Chem.-Eur. J. 2013, 19, 5232-5237 10.1002/chem.201300052
144. Haibach, M. C.; Deb, I.; De, C. K.; Seidel, D. Redox-Neutral Indole Annulation Cascades J. Am. Chem. Soc. 2011, 133, 2100-2103 10.1021/ja110713k
145. 3)-H Bond Functionalization Adv. Synth. Catal. 2015, 357, 901-906 10.1002/adsc.201400775
146. Pahadi, N. K.; Paley, M.; Jana, R.; Waetzig, S. R.; Tunge, J. A. Formation of N-Alkylpyrroles via Intermolecular Redox Amination J. Am. Chem. Soc. 2009, 131, 16626-16627 10.1021/ja907357g
147. Xue, X.; Yu, A.; Cai, Y.; Cheng, J.-P. A Computational Reinvestigation of the Formation of N-Alkylpyrroles via Intermolecular Redox Amination Org. Lett. 2011, 13, 6054-6057 10.1021/ol2025247
148. Mao, H.; Xu, R.; Wan, J.; Jiang, Z.; Sun, C.; Pan, Y. Tunable Hydride Transfer in the Redox Amination of Indoline with Aldehyde: An Attractive Intramolecular Hydrogen-Bond Effect Chem.-Eur. J. 2010, 16, 13352-13355 10.1002/chem.201001896
149. Yu, Y.; Wang, C.; He, X.; Yao, X.; Zu, L. Efficient Assembly of Polysubstituted Pyrroles via a (3 + 2) Cycloaddition/Skeletal Rearrangement/Redox Isomerization Cascade Reaction Org. Lett. 2014, 16, 3580-3583 10.1021/ol501580b
150. Chen, W.; Seidel, D. The Redox-Mannich Reaction Org. Lett. 2014, 16, 3158-3161 10.1021/ol501365j
151. Richers, M. T.; Breugst, M.; Platonova, A. Y.; Ullrich, A.; Dieckmann, A.; Houk, K. N.; Seidel, D. Redox-Neutral α-Oxygenation of Amines: Reaction Development and Elucidation of the Mechanism J. Am. Chem. Soc. 2014, 136, 6123-6135 10.1021/ja501988b
152. Dieckmann, A.; Richers, M. T.; Platonova, A. Y.; Zhang, C.; Seidel, D.; Houk, K. N. Metal-Free α-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates J. Org. Chem. 2013, 78, 4132-4144 10.1021/jo400483h
153. Jarvis, C. L.; Richers, M. T.; Breugst, M.; Houk, K. N.; Seidel, D. Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals Org. Lett. 2014, 16, 3556-3559 10.1021/ol501509b
154. Das, D.; Seidel, D. Redox-Neutral α-C-H Bond Functionalization of Secondary Amines with Concurrent C-P Bond Formation/N-Alkylation Org. Lett. 2013, 15, 4358-4361 10.1021/ol401858k
155. Kabachnik, M. I.; Medved, T. Y. Dokl. Akad. Nauk SSSR 1952, 83, 689
156. Fields, E. K. The Synthesis of Esters of Substituted Amino Phosphonic Acids J. Am. Chem. Soc. 1952, 74, 1528 10.1021/ja01126a054
157. Mantelingu, K.; Lin, Y.; Seidel, D. Intramolecular [3 + 2]-Cycloadditions of Azomethine Ylides Derived from Secondary Amines via Redox-Neutral C-H Functionalization Org. Lett. 2014, 16, 5910-5913 10.1021/ol502918g
158. Davies, H. M. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, pp 1031-1067.
159. Davies, H. M. L.; Smith, H. D.; Hu, B.; Klenzak, S. M.; Hegner, F. J. Divergent Reaction Pathways Between Rhodium(II)-Stabilized Vinylcarbenoids and Benzenes J. Org. Chem. 1992, 57, 6900-6903 10.1021/jo00051a041
160. 2-Symmetric Anilines Org. Lett. 2004, 6, 1769-1772 10.1021/ol0495467
161. Park, C. P.; Nagle, A.; Yoon, C. H.; Chen, C.; Jung, K. W. Formal Aromatic C-H Insertion for Stereoselective Isoquinolinone Synthesis and Studies on Mechanistic Insights into the C-C Bond Formation J. Org. Chem. 2009, 74, 6231-6236 10.1021/jo9011255
162. Tayama, E.; Ishikawa, M.; Iwamoto, H.; Hasegawa, E. Copper(II)-Acid Co-Catalyzed Intermolecular Substitution of Electron-Rich Aromatics with Diazoesters Tetrahedron Lett. 2012, 53, 5159-5161 10.1016/j.tetlet.2012.07.070
163. Zhai, C.; Xing, D.; Jing, C.; Zhou, J.; Wang, C.; Wang, D.; Hu, W. Facile Synthesis of 3-Aryloxindoles via Brønsted Acid Catalyzed Friedel-Crafts Alkylation of Electron-Rich Arenes with 3-Diazooxindoles Org. Lett. 2014, 16, 2934-2937 10.1021/ol5010752
164. Ishihara, K.; Hasegawa, A.; Yamamoto, H. Polystyrene-Bound Tetrafluorophenylbis(triflyl)methane as an Organic-Solvent-Swellable and Strong Brønsted Acid Catalyst Angew. Chem., Int. Ed. 2001, 40, 4077-4079 10.1002/1521-3773(20011105)40:214077::AID-ANIE40773.0.CO;2-1
165. Ishihara, K.; Hasegawa, A.; Yamamoto, H. Single-Pass Reaction Column System with Super Brønsted Acid-loaded Resin Synlett 2002, 1296-1298 10.1055/s-2002-32964
166. Ishihara, K.; Hasegawa, A.; Yamamoto, H. A Fluorous Super Brønsted Acid Catalyst: Application to Fluorous Catalysis without Fluorous Solvents Synlett 2002, 1299-1301 10.1055/s-2002-32965
167. Hasegawa, A.; Ishihara, K.; Yamamoto, H. Trimethylsilyl Pentafluorophenylbis(trifluoromethanesulfonyl)methide as a Super Lewis Acid Catalyst for the Condensation of Trimethylhydroquinone with Isophytol Angew. Chem., Int. Ed. 2003, 42, 5731-5733 10.1002/anie.200352382
168. Hasegawa, A.; Ishikawa, T.; Ishihara, K.; Yamamoto, H. Facile Synthesis of Aryl- and Alkyl-bis(trifluoromethylsulfonyl)methanes Bull. Chem. Soc. Jpn. 2005, 78, 1401-1410 10.1246/bcsj.78.1401
169. Hasegawa, A.; Naganawa, Y.; Fushimi, M.; Ishihara, K.; Yamamoto, H. Design of Brønsted Acid-Assisted Chiral Brønsted Acid Catalyst Bearing a Bis(triflyl)methyl Group for a Mannich-Type Reaction Org. Lett. 2006, 8, 3175-3178 10.1021/ol060939a
170. Koshar, R. J.; Barber, L. L., Jr. U.S. Patent 4,053,519, 1977.
171. Takahashi, A.; Yanai, H.; Taguchi, T. Tetrakis(trifluoromethanesulfonyl)propane: Highly Effective Brønsted Acid Catalyst for Vinylogous Mukaiyama-Michael Reaction of α,β-Enones with Silyloxyfurans Chem. Commun. 2008, 2385-2387 10.1039/b800815a
172. Takahashi, A.; Yanai, H.; Zhang, M.; Sonoda, T.; Mishima, M.; Taguchi, T. Highly Effective Vinylogous Mukaiyama-Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane J. Org. Chem. 2010, 75, 1259-1265 10.1021/jo902641g
173. Yanai, H.; Taguchi, T. Synthesis and Catalysis of Strong Carbon Acids Containing Bis(triflyl)methyl Group Yuki Gosei Kagaku Kyokaishi 2014, 72, 158-170 10.5059/yukigoseikyokaishi.72.158
174. Chen, J.; Gao, P.; Yu, F.; Yang, Y.; Zhu, S.; Zhai, H. Total Synthesis of (±)-Merrilactone A Angew. Chem., Int. Ed. 2012, 51, 5897-5899 10.1002/anie.201200378
175. Yanai, H.; Yoshino, Y.; Takahashi, A.; Taguchi, T. Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones J. Org. Chem. 2010, 75, 5375-5378 10.1021/jo100915e
176. Yanai, H.; Takahashi, A.; Taguchi, T. 1,4-Addition of Silicon Dienoates to α,β-Unsaturated Aldehydes Catalyzed by in situ-Generated Silicon Lewis Acid Chem. Commun. 2010, 46, 8728-8730 10.1039/c0cc02438d
177. 2-Catalyzed Vinylogous Mukaiyama Aldol Reaction of 2-(Trimethylsiloxy)furans with Aldehydes J. Org. Chem. 2005, 70, 3654-3659 10.1021/jo0501339
178. For the effect of conjugate base, see: Hiraiwa, Y.; Ishihara, K.; Yamamoto, H. Crucial Role of the Conjugate Base for Silyl Lewis Acid Induced Mukaiyama Aldol Reactions Eur. J. Org. Chem. 2006, 2006, 1837-1844 10.1002/ejoc.200500845
179. Yanai, H.; Ogura, H.; Fukaya, H.; Kotani, A.; Kusu, F.; Taguchi, T. An Effective Method to Introduce Carbon Acid Functionality: 2,2-Bis(trifluoromethanesulfonyl)ethylation Reaction of Arenes Chem.-Eur. J. 2011, 17, 11747-11751 10.1002/chem.201102023
180. Yanai, H.; Taguchi, T. Organic Acid Induced Olefination Reaction of Lactones Chem. Commun. 2012, 48, 8967-8969 10.1039/c2cc33606e
181. Yanai, H.; Ishii, N.; Matsumoto, T.; Taguchi, T. Organic Acid Catalysts in Reactions of Lactones with Silicon Enolates Asian J. Org. Chem. 2013, 2, 989-996 10.1002/ajoc.201300157
182. Yanai, H.; Fujita, M.; Taguchi, T. A Regioselective Synthesis of Poly-Substituted Aryl Triflones Through Self-Promoting Three Component Reaction Chem. Commun. 2011, 47, 7245-7247 10.1039/c1cc12093j
183. Barber, H. J.; Smiles, S. CXLV.-Cyclic Disulphides Derived from Diphenyl J. Chem. Soc. 1928, 1141-1149 10.1039/jr9280001141
184. Kampen, D.; Ladépêche, A.; Claßen, G.; List, B. Brønsted Acid-Catalyzed Three-Component Hosomi-Sakurai Reactions Adv. Synth. Catal. 2008, 350, 962-966 10.1002/adsc.200800036
185. Hatano, M.; Maki, T.; Moriyama, K.; Arinobe, M.; Ishihara, K. Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction J. Am. Chem. Soc. 2008, 130, 16858 10.1021/ja806875c
186. Takahashi, K. Jpn. Kokai Tokkyo Koho JP2008-262585, 2008.
187. García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. A Powerful Chiral Counteranion Motif for Asymmetric Catalysis Angew. Chem., Int. Ed. 2009, 48, 4363-4366 10.1002/anie.200901768
188. For a review of chiral sulfonimide, see: van Gemmeren, M.; Lay, F.; List, B. Aldrichimica Acta 2014, 47, 3-13
189. Treskow, M.; Neudörfl, J.; Giernoth, R. BINBAM-A New Motif for Strong and Chiral Brønsted Acids Eur. J. Org. Chem. 2009, 2009, 3693-3697 10.1002/ejoc.200900548
190. He, H.; Chen, L.-Y.; Wong, W.-Y.; Chan, W.-H.; Lee, A. W. M. Practical Synthetic Approach to Chiral Sulfonimides (CSIs)-Chiral Brønsted Acids for Organocatalysis Eur. J. Org. Chem. 2010, 2010, 4181-4184 10.1002/ejoc.201000477
191. Hatano, M.; Ozaki, T.; Nishikawa, K.; Ishihara, K. Synthesis of Optically Pure 3,3′-Diaryl Binaphthyl Disulfonic Acids via Stepwise N-S Bond Cleavage J. Org. Chem. 2013, 78, 10405 10.1021/jo401848z
192. For example, see: Bandini, M.; Melloni, A.; Umani-Ronchi, A. New Catalytic Approaches in the Stereoselective Friedel-Crafts Alkylation Reaction Angew. Chem., Int. Ed. 2004, 43, 550-556 10.1002/anie.200301679
193. Li, G.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C. Organocatalytic Enantioselective Friedel-Crafts Reaction of Pyrrole Derivatives with Imines Org. Lett. 2007, 9, 4065-4068 10.1021/ol701881j
194. Nakamura, S.; Sakurai, Y.; Nakashima, H.; Shibata, N.; Toru, T. Organocatalytic Enantioselective Aza-Friedel-Crafts Alkylation of Pyrroles with N-(Heteroarenesulfonyl)imines Synlett 2009, 2009, 1639-1642 10.1055/s-0029-1217324
195. Hatano, M.; Sugiura, Y.; Akakura, M.; Ishihara, K. S. Enantioselective Friedel-Crafts Aminoalkylation Catalyzed by Chiral Ammonium 1,1′-Binaphthyl-2,2′-disulfonates Synlett 2011, 2011, 1247-1250 10.1055/s-0030-1260538
196. Goodman, M.; Chorev, M. On the Concept of Linear Modified Retro-Peptide Structures Acc. Chem. Res. 1979, 12, 1-7 10.1021/ar50133a001
197. Chorev, M.; Goodman, M. A Dozen Years of Retro-Inverso Peptidomimetics Acc. Chem. Res. 1993, 26, 266-273 10.1021/ar00029a007
198. Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. Brønsted Acid-Catalyzed Imine Amidation J. Am. Chem. Soc. 2005, 127, 15696-15697 10.1021/ja0533085
199. Liang, Y.; Rowland, E. B.; Rowland, R. B.; Perman, J. A.; Antilla, J. C. VAPOL Phosphoric Acid Catalysis: the Highly Enantioselective Addition of Imides to Imines Chem. Commun. 2007, 4477-4479 10.1039/b709276h
200. Cheng, X.; Vellalath, S.; Goddard, R.; List, B. Direct Catalytic Asymmetric Synthesis of Cyclic Aminals from Aldehydes J. Am. Chem. Soc. 2008, 130, 15786-15787 10.1021/ja8071034
201. Rueping, M.; Antonchick, A. P.; Sugiono, E.; Grenader, K. Asymmetric Brønsted Acid Catalysis: Catalytic Enantioselective Synthesis of Highly Biologically Active Dihydroquinazolinones Angew. Chem., Int. Ed. 2009, 48, 908-910 10.1002/anie.200804770
202. Hatano, M.; Ozaki, T.; Sugiura, Y.; Ishihara, K. Enantioselective Direct Aminalization with Primary Carboxamides Catalyzed by Chiral Ammonium 1,1′-Binaphthyl-2,2′-disulfonates Chem. Commun. 2012, 48, 4986-4988 10.1039/c2cc31530k
203. Ratjen, L.; García-García, P.; Lay, F.; Beck, M. E.; List, B. Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions Angew. Chem., Int. Ed. 2011, 50, 754-758 10.1002/anie.201005954
204. Guin, J.; Rabalakos, C.; List, B. Highly Enantioselective Hetero-Diels-Alder Reaction of 1,3-Bis(silyloxy)-1,3-dienes with Aldehydes Catalyzed by Chiral Disulfonimide Angew. Chem., Int. Ed. 2012, 51, 8859-8863 10.1002/anie.201204262
205. Mahlau, M.; García-García, P.; List, B. Asymmetric Counteranion-Directed Catalytic Hosomi-Sakurai Reaction Chem.-Eur. J. 2012, 18, 16283-16287 10.1002/chem.201203623
206. Gandhi, S.; List, B. Catalytic Asymmetric Three-Component Synthesis of Homoallylic Amines Angew. Chem., Int. Ed. 2013, 52, 2573-2576 10.1002/anie.201209776
207. 3-Amino Esters Directly from N-Boc-Amino Sulfones J. Am. Chem. Soc. 2013, 135, 15334-15337 10.1021/ja408747m
208. Wang, Q.; van Gemmeren, M.; List, B. Asymmetric Disulfonimide-Catalyzed Synthesis of δ-Amino-β-Ketoester Derivatives by Vinylogous Mukaiyama-Mannich Reactions Angew. Chem., Int. Ed. 2014, 53, 13592-13595 10.1002/anie.201407532
209. Gröger, H.; Hammer, B. Catalytic Concepts for the Enantioselective Synthesis of α-Amino and α-Hydroxy Phosphonates Chem.-Eur. J. 2000, 6, 943-948 10.1002/(SICI)1521-3765(20000317)6:6943::AID-CHEM9433.0.CO;2-4
210. Ma, J.-A. Catalytic Asymmetric Synthesis of α- and β-Amino Phosphonic Acid Derivatives Chem. Soc. Rev. 2006, 35, 630-636 10.1039/b517100h
211. Merino, P.; Marqués-López, E.; Herrera, R. P. Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines Adv. Synth. Catal. 2008, 350, 1195-1208 10.1002/adsc.200800131
212. Bhadury, P. S.; Li, H. Organocatalytic Asymmetric Hydrophosphonylation/Mannich Reactions Using Thiourea, Cinchona and Brønsted Acid Catalysts Synlett 2012, 23, 1108-1131 10.1055/s-0031-1290193
213. Doak, G. O.; Freedman, L. D. The Structure and Properties of the Dialkyl Phosphonates Chem. Rev. 1961, 61, 31-44 10.1021/cr60209a002
214. Pietro, W. J.; Hehre, W. J. Tautomerization of Dimethyl Phosphonate J. Am. Chem. Soc. 1982, 104, 3594-3595 10.1021/ja00377a009
215. Schlemminger, I.; Saida, Y.; Gröger, H.; Maison, W.; Durot, N.; Sasai, H.; Shibasaki, M.; Martens, J. Concept of Improved Rigidity: How to Make Enantioselective Hydrophosphonylation of Cyclic Imines Catalyzed by Chiral Heterobimetallic Lanthanoid Complexes Almost Perfect J. Org. Chem. 2000, 65, 4818-4825 10.1021/jo991882r
216. Abramov, V. S. Dokl. Akad. Nauk SSSR 1950, 73, 487
217. Abramov, V. S. Dokl. Akad. Nauk SSSR 1954, 95, 991
218. Wozniak, L.; Chojnowski, J. Silyl Esters of Phosphorous-Common Intermediates in Synthesis Tetrahedron 1989, 45, 2465-2524 10.1016/S0040-4020(01)80083-1
219. Guin, J.; Wang, Q.; van Gemmeren, M.; List, B. The Catalytic Asymmetric Abramov Reaction Angew. Chem., Int. Ed. 2015, 54, 355-358 10.1002/anie.201409411
220. Ratjen, L.; van Gemmeren, M.; Pesciaioli, F.; List, B. Towards High-Performance Lewis Acid Organocatalysis Angew. Chem., Int. Ed. 2014, 53, 8765-8769 10.1002/anie.201402765
221. Chen, L.-Y.; He, H.; Chan, W.-H.; Lee, A. W. M. Chiral Sulfonimide as a Brønsted Acid Organocatalyst for Asymmetric Friedel-Crafts Alkylation of Indoles with Imines J. Org. Chem. 2011, 76, 7141-7147 10.1021/jo2011335
222. Prévost, S.; Dupré, N.; Leutzsch, M.; Wang, Q.; Wakchaure, V.; List, B. Catalytic Asymmetric Torgov Cyclization: A Concise Total Synthesis of (+)-Estrone Angew. Chem., Int. Ed. 2014, 53, 8770-8773 10.1002/anie.201404909
223. Hashimoto, T. Brønsted Acids: Brønsted Acid Catalysts Other than Phosphoric Acids. In Asymmetric Organocatalysis 2: Brønsted Base and Acid Catalysts, and Additional Topics; Maruoka, K., Ed.; Georg Thieme Verlag: Stuttgart, New York, 2012; Vol. 2, pp 279-296.
224. Momiyama, N.; Yamamoto, H. Brønsted Acid Catalysis of Achiral Enamine for Regio- and Enantioselective Nitroso Aldol Synthesis J. Am. Chem. Soc. 2005, 127, 1080-1081 10.1021/ja0444637
225. Hashimoto, T.; Maruoka, K. Design of an Axially Chiral Dicarboxylic Acid and Its Application in Syntheses of Optically Active β-Amino Acids and β-Amino Phosphonic Acid Derivatives Synthesis 2008, 2008, 3703-3706 10.1055/s-0028-1083212
226. 2-Symmetric Chiral Quaternary Ammonium Bromides J. Org. Chem. 2003, 68, 4576-4578 10.1021/jo030032f
227. For a review of acid-catalyzed reaction of diazocarbonyl compounds, see: Hashimoto, T.; Maruoka, K. Development of Synthetic Transformations by Control of Acid-Catalyzed Reactions of Diazocarbonyl Compounds Bull. Chem. Soc. Jpn. 2013, 86, 1217-1230 10.1246/bcsj.20130164
228. Hashimoto, T.; Maruoka, K. Design of Axially Chiral Dicarboxylic Acid for Asymmetric Mannich Reaction of Arylaldehyde N-Boc Imines and Diazo Compounds J. Am. Chem. Soc. 2007, 129, 10054-10055 10.1021/ja0713375
229. Hashimoto, T.; Kimura, H.; Nakatsu, H.; Maruoka, K. Synthetic Application and Structural Elucidation of Axially Chiral Dicarboxylic Acid: Asymmetric Mannich-type Reaction with Diazoacetate, (Diazomethyl)phosphonate, and (Diazomethyl)sulfone J. Org. Chem. 2011, 76, 6030-6037 10.1021/jo2005999
230. Uraguchi, D.; Sorimachi, K.; Terada, M. Organocatalytic Asymmetric Direct Alkylation of α-Diazoester via C-H Bond Cleavage J. Am. Chem. Soc. 2005, 127, 9360-9361 10.1021/ja051922a
231. Antilla, J. C.; Wulff, W. D. Catalytic Asymmetric Aziridination with Arylborate Catalysts Derived from VAPOL and VANOL Ligands Angew. Chem., Int. Ed. 2000, 39, 4518-4521 10.1002/1521-3773(20001215)39:244518::AID-ANIE45183.3.CO;2-A
232. Hashimoto, T.; Hirose, M.; Maruoka, K. Asymmetric Imino Aza-enamine Reaction Catalyzed by Axially Chiral Dicarboxylic Acid: Use of Arylaldehyde N,N-Dialkylhydrazones as Acyl Anion Equivalent J. Am. Chem. Soc. 2008, 130, 7556-7557 10.1021/ja802704j
233. Hashimoto, T.; Kimura, H.; Maruoka, K. Enantioselective Formal Alkenylations of Imines Catalyzed by Axially Chiral Dicarboxylic Acid Using Vinylogous Aza-Enamines Angew. Chem., Int. Ed. 2010, 49, 6844-6847 10.1002/anie.201003600
234. Hashimoto, T.; Kimura, H.; Kawamata, Y.; Maruoka, K. Generation and Exploitation of Acyclic Azomethine Imines in Chiral Brønsted Acid Catalysis Nat. Chem. 2011, 3, 642-646 10.1038/nchem.1096
235. Hashimoto, T.; Uchiyama, N.; Maruoka, K. Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid J. Am. Chem. Soc. 2008, 130, 14380-14381 10.1021/ja805635c
236. Pan, S. C.; List, B. Catalytic Three-Component Ugi Reaction Angew. Chem., Int. Ed. 2008, 47, 3622-3625 10.1002/anie.200800494
237. Yue, T.; Wang, M.-X.; Wang, D.-X.; Masson, G.; Zhu, J. Brønsted Acid Catalyzed Enantioselective Three-Component Reaction Involving the α Addition of Isocyanides to Imines Angew. Chem., Int. Ed. 2009, 48, 6717-6721 10.1002/anie.200902385
238. Hashimoto, T.; Kimura, H.; Kawamata, Y.; Maruoka, K. A Catalytic Asymmetric Ugi-type Reaction With Acyclic Azomethine Imines Angew. Chem., Int. Ed. 2012, 51, 7279-7281 10.1002/anie.201201905
239. Hashimoto, T.; Nakatsu, H.; Takiguchi, Y.; Maruoka, K. Axially Chiral Dicarboxylic Acid Catalyzed Activation of Quinone Imine Ketals: Enantioselective Arylation of Enecarbamates J. Am. Chem. Soc. 2013, 135, 16010-16013 10.1021/ja407501h
240. Sugiura, M.; Tokudomi, M.; Nakajima, M. Enantioselective Conjugate Addition of Boronic Acids to Enones Catalyzed by O-Monoacyltartaric Acids Chem. Commun. 2010, 46, 7799-7800 10.1039/c0cc03076g
241. Grimblat, N.; Sugiura, M.; Pellegrinet, S. C. A Hydrogen Bond Rationale for the Enantioselective β-Alkenylboration of Enones Catalyzed by O-Monoacyltartaric Acids J. Org. Chem. 2014, 79, 6754-6758 10.1021/jo5012398
242. Sugiura, M.; Kinoshita, R.; Nakajima, M. O-Monoacyltartaric Acid Catalyzed Enantioselective Conjugate Addition of a Boronic Acid to Dienones: Application to the Synthesis of Optically Active Cyclopentenones Org. Lett. 2014, 16, 5172-5175 10.1021/ol502526y
243. Kodama, T.; Moquist, P. N.; Schaus, S. E. Enantioselective Boronate Additions to N-Acyl Quinoliniums Catalyzed by Tartaric Acid Org. Lett. 2011, 13, 6316-6319 10.1021/ol2028702
244. Yamaoka, Y.; Miyabe, H.; Takemoto, Y. Catalytic Enantioselective Petasis-Type Reaction of Quinolines Catalyzed by a Newly Designed Thiourea Catalyst J. Am. Chem. Soc. 2007, 129, 6686-6687 10.1021/ja071470x
245. Auvil, T. J.; Mattson, A. E. Internal Lewis Acid Assisted Benzoic Acid Catalysis Synthesis 2012, 44, 2173-2180 10.1055/s-0031-1291048
246. Hashimoto, T.; Gálvez, A. O.; Maruoka, K. In Situ Assembled Boronate Ester Assisted Chiral Carboxylic Acid Catalyzed Asymmetric Trans-Aziridinations J. Am. Chem. Soc. 2013, 135, 17667-17670 10.1021/ja407764u