Noncovalent bifunctional organocatalysis mediated by β-amino alcohols

Current Organic Chemistry

Volumn 15, Issue 13, 2011, Pages 2147-2183

  della Sala, Giorgio ^a   Russo, Alessio ^a   Lattanzi, Alessandra ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Carbon heteroatom bond forming reactions; Carboncarbon bond forming reactions; Cinchona alkaloids; Enantioselective organocatalysis; Noncovalent catalysis; , diaryl prolinols; amino alcohols

Indexed keywords

ADDITION REACTIONS; ALKALOIDS; CARBONYL COMPOUNDS; CATALYSIS; ENANTIOSELECTIVITY; HYDROGEN BONDS; ORGANOCATALYST;

BOND-FORMING REACTIONS; CARBON-CARBON BOND-FORMING REACTIONS; CARBON-HETEROATOM BOND FORMING REACTION; CARBON-HETEROATOM BONDS; CINCHONA ALKALOID; ENANTIOSELECTIVE ORGANOCATALYSIS; NONCOVALENT; NONCOVALENT CATALYSE; Α, Α-DIARYL PROLINOL; Β-AMINO ALCOHOL;

AMINO ALCOHOLS;

EID: 79959322320     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211796150741     Document Type: Review

References (240)

1. For selected reviews and books, see: a) Dalko, P. I.; Moisan, L. Enantioselective organocatalysis. Angew. Chem., Int. Ed., 2001, 40, 3726-3748.
2. Dalko, P. I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem., Int. Ed., 2004, 43, 5138-5175.
3. Houk, K. N.; List, B.; Guest Eds.; Acc. Chem. Res., 2004, 37, 487 (thematic issue on Asymmetric Organocatalysis).
4. Asymmetric Organocatalysis: from Biomimetic Concepts to Applications in Asymmetric Synthesis, (Eds.: Berkessel, A. Gröger, H.), Wiley-VCH, Weinheim, 2005.
5. Enantioselective Organocatalysis: Reactions and Experimental Procedures, (Ed.: Dalko, P. I.), Wiley-VCH, Weinheim, 2007.
6. Mac-Millan,D. W. C. The advent and the development of organocatalysis. Nature, 2008, 455, 304-308.
7. Dondoni, A.; Massi, A. Asymmetric organocatalysis: from infancy to adolescence. Angew. Chem., Int. Ed., 2008, 47, 4638-4660.
8. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Asymmetric aminocatalysis-gold rush in organic chemistry. Angew. Chem., Int. Ed., 2008, 47, 6138-6171.
9. Asymmetric Organocatalysis, (Ed.: B. List), Springer- Verlag, 2009.
10. For selected reviews and books on cinchona alkaloids and their derivatives, see: a) Kacprzak, K.; Gawronski, J. Cinchona alkaloids and their derivatives: versatile catalysts and ligands in asymmetric synthesis. Synthesis, 2001, 961-998.
11. Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Asymmetric organic catalysis with modified cinchona alkaloids. Acc. Chem. Res., 2004, 37, 621-631.
12. Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Cupreines and cupreidines: an emerging class of bifunctional Cinchona organocatalysts. Angew. Chem., Int. Ed., 2006, 45, 7496-7504.
13. Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, (Ed. Song, C. E.), Wiley-VCH, Weinheim, 2009.
14. Marcelli, T.; Hiemstra, H. Cinchona alkaloids in asymmetric organocatalysis. Synthesis, 2010, 1229-1279.
15. For reviews on L-proline derivatives, see: Jarvo, E. R.; Miller, S. J. Aminoacids and peptides as asymmetric organocatalysts. Tetrahedron, 2002, 58, 2481-2495.
16. List, B. Proline-catalysed asymmetric reactions. Tetrahedron, 2002, 58, 5573-5590.
17. a) Hiemstra, H.; Wynberg, H. Addition of aromatic thiols to conjugated cycloalkenones, catalysed by chiral β-hydroxy amines. A mechanistic study of homogeneous catalytic asymmetric synthesis. J. Am. Chem. Soc., 1981, 103, 417-430.
18. Cucinotta, C. S.; Kosa, M.; Melchiorre, P.; Cavalli, A.; Gervasio, F. L. Bifunctional catalysis by natural cinchona alkaloids: a mechanism explained. Chem. Eur. J., 2009, 15, 7913-7921.
19. Hydrogen Bonding in Organic Synthesis, (Ed. Pihko P. M.), Wiley-VCH, Weinheim, 2009.
20. a) List, B. Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents. Acc. Chem. Res., 2004, 37, 548-557.
21. Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.-Y., Houk, K. N. Theory of asymmetric organocatalysis of aldol and related reactions: rationalizations and predictions. Acc. Chem. Res., 2004, 37, 558-569.
22. Notz, W.; Tanaka, F.; Barbas, III C. F. Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric aldol, Mannich, Michael, and Diels-Alder reactions. Acc. Chem. Res., 2004, 37, 580-591.
23. Seayad, J.; List, B. Asymmetric organocatalysis. Org. Biomol. Chem., 2005, 3, 719-724.
24. Erkkilä, A.; Majander, I.; Pihko, P. M. Iminium catalysis. Chem. Rev., 2007, 107, 5416-5470.
25. Bartoli, G.; Melchiorre, P. A novel organocatalytic tool for the iminium activation of α, β-unsaturated ketones. Synlett, 2008, 1759-1772.
26. Xu, L.-W.; Luo, J.; Lu, Y. Asymmetric catalysis with chiral primary amine-based organocatalysts. Chem. Commun., 2009, 1807-1821.
27. For reviews, see: a) Connon, S. J. Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts. Chem. Commun., 2008, 2499-2510.
28. Yu, X.; Wang, W. Hydrogen-bond-mediated asymmetric catalysis. Chem. Asian J., 2008, 3, 516-532.
29. a) Malerich, J. P.; Hagihara, K.; Rawal, V. H. Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. J. Am. Chem. Soc., 2008, 130, 14416-14417.
30. Xu, D.-Q.; Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhong, A.- G.; Xia, A.-B.; Xu, Z.-Y. Chiral squaramides as highly enantioselective catalysts for Michael addition reactions of 4-hydroxycoumarins and 4- hydroxypyrone to β, γ-unsaturated α -keto esters. Chem. Eur. J., 2010, 16, 4177-4180.
31. For a review, see: Lattanzi, A. α, α -Diaryl prolinols: bifunctional organocatalysts for asymmetric synthesis. Chem Commun., 2009, 1452-1463.
32. For reviews on bifunctional organocatalysis, see: a) Liu, X.; Lin, L.; Feng, X. Amide-based bifunctional organocatalysts in asymmetric reactions. Chem. Commun., 2009, 6145-6158.
33. Palomo, C.; Oiarbide. M.; López, R. Asymmetric organocatalysis by chiral Brønsted bases: implications and applications. Chem. Soc. Rev., 2009, 38, 632-653.
34. Bhadury, P. S.; Song, B.-A.; Yang, S.; Hu, D.-Y.; Xue, W. Bifunctional chiral organocatalysts in organic transformations. Curr. Org. Synth., 2009, 6, 380-399.
35. For reviews, see: a) Marigo, M.; Jørgensen, K. A. Organocatalytic direct asymmetric α -heteroatom functionalization of aldehydes and ketones. Chem. Commun., 2006, 2001-2011.
36. Palomo, C.; Mielgo, A. Diaryl prolinol ethers: expanding the potential of enamine/iminium-ion catalysis. Angew. Chem., Int. Ed., 2006, 45, 7876-7880.
37. Mielgo, A.; Palomo, C. α, α -Diaryl prolinol ethers: new tools for functionalization of carbonyl compounds. Chem. Asian J., 2008, 3, 922-948.
38. For reviews, see: a) Merino, P.; Marqués-López, E.; Herrera, R. P. Catalytic enantioselective hydrophosphonylation of aldehydes and imines. Adv. Synth. Catal., 2008, 350, 1195-1208.
39. Ordóñez, M.; Rojas-Cabrera, H.; Cativiela, C. An overview of stereoselective synthesis of α -aminophosphonic acids and derivatives. Tetrahedron, 2009, 65, 17-49.
40. Albrecht, Ł.; Albrecht, A.; Krawczyk, H.; Jørgensen, K. A. Organocatalytic asymmetric synthesis of organophosphorus compounds. Chem. Eur. J., 2010, 16, 28-48.
41. a) Aminophosphonic and Aminophosphinic Acids, (Eds.: Kukhar, V. P., Hudson, H. R.), John Wiley & Sons, New York, 2000.
42. Wiemer, D. F. Synthesis of nonracemic phosphonates. Tetrahedron, 1997, 53, 16609-16644.
43. Fields, S. C. Synthesis of natural products containing a C-P bond. Tetrahedron, 1999, 55, 12237-12273.
44. a) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J. Med. Chem., 1989, 32, 1652-1661.
45. Ding, J.; Fraser, M. E.; Meyer, J. H.; Bartlett, P. A.; James, M. N. G. Macrocyclic inhibitors of penicillopepsin. 2. X-ray crystallographic analyses of penicillopepsin complexed with a P3 - P1 macrocyclic peptidyl inhibitor and with its two acyclic analogues. J. Am. Chem. Soc., 1998, 120, 4610-4621.
46. Smith, W. W.; Bartlett, P. A. Macrocyclic inhibitors of penicillopepsin. 3. Design, synthesis, and evaluation of an inhibitor bridged between P2 and P1'. J. Am. Chem. Soc., 1998, 120, 4622-4628.
47. a) Atherton, F. R.; Hassall, C. H.; Lambert, R. W. Synthesis and structureactivity relationships of antibacterial phosphonopeptides incorporating (1- aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. J. Med. Chem., 1986, 29, 29-40.
48. Alonso, E.; Alonso, E.; Solis, A.; del Pozo, C. Synthesis of N-alkyl-(a-aminoalkyl)phosphine oxides and phosphonic esters as potential HIV-protease inhibitors, starting from α -aminoacids. Synlett, 2000, 698-700.
49. a) Gröger, H.; Hammer, B. Catalytic concepts for the enantioselective synthesis of α -amino and α -hydroxy phosphonates. Chem. Eur. J., 2000, 943-948.
50. Kukhar, V. P.; Soloshonok, V. H.; Solodenko, V. A. Asymmetric synthesis of phosphorus analogs of amino acids. Phosphorus, Sulfur Silicon, 1994, 92, 239-264.
51. Yokomatsu, T.; Yamgishi, T.; Shibuya, S. Enantioselective hydrophosphonylation of aromatic aldehydes catalysed by chiral titanium alkoxides. Tetrahedron: Asymmetry, 1993, 4, 1779-1782.
52. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. New homochiral cyclic diol ligands for titanium alkoxide catalysed phosphonylation of aldehydes. Tetrahedron Lett., 1998, 39, 5485-5488.
53. Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. Catalytic asymmetric synthesis of α -hydroxy phosphonates using the Al-Li-BINOL complex. J. Org.Chem., 1996, 61, 2926-2927.
54. Duxbury, J. P.; Cawley, A.; Thornton-Pett, M.; Wantz, L.; Warne, J. N. D.; Greatrex, R.; Brown, D.; Kee, T. P. Chiral aluminium complexes as phospho-transfer catalysts. Tetrahedron Lett., 1999, 40, 4403-4406.
55. a) Wynberg, H.; Smaardijk, A. A. Asymmetric catalysis in carbonphosphorus bond formation. Tetrahedron Lett., 1983, 24, 5899-5900.
56. Smaardijk, A. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H. The absolute configuration of α -hydroxyphosphonates. Tetrahedron Lett., 1985, 26, 493-496.
57. Joly, G. D.; Jacobsen, E. N. Thiourea-catalysed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched α -amino phosphonic acids. J. Am. Chem. Soc., 2004, 126, 4102-4103.
58. Pettersen, D.; Marcolini, M.; Bernardi, L.; Fini, F.; Herrera, R. P.; Sgarzani, V.; Ricci A. Direct access to enantiomerically enriched α -amino phosphonic acid derivatives by organocatalytic asymmetric hydrophosphonylation of imines. J. Org. Chem., 2006, 71, 6269-6272.
59. Springs, B.; Haake, P. The mechanism of amine-catalysed halohydrin formation from α -chloro ketones and phosphonate diesters. J. Org. Chem., 1977, 42, 472-474.
60. Nakamura, S.; Nakashima, H.; Yamamura, A.; Shibata, N.; Toru, T. Organocatalytic enantioselective hydrophosphonylation of sulfonylimines having a heteroarenesulfonyl group as a novel stereocontroller. Adv. Synth. Catal., 2008, 350, 1209-1212.
61. Nakamura, S.; Hayashi, M.; Hiramatsu, Y.; Shibata, N.; Funahashi, Y.; Toru, T. Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids. J. Am. Chem. Soc., 2009, 131, 18240-18241.
62. Mikołajczyk, M.; Drabowicz, J.; Lyzùwa, P. In Enantioselective Synthesis of β -Amino Acids, 2nd Ed., (Eds.: Juaristi, E., Soloshonok, V. A.), John Wiley, Hoboken, 2005; chapter 12.
63. For a review, see: Kukhar, V. P. In Aminophosphonic and Aminophosphinic Acids-Chemistry and Biological Activity, (Eds.: Kukhar, V. P., Hudson, H. R.), John Wiley, Chichester, 2000; pp 127-172.
64. Cravotto, G.; Giovenzana, G. B.; Pagliarin, R.; Palmisano, G.; Sisti, M. A straightforward entry into enantiomerically enriched β -amino- α -hydroxyphosphonic acid derivatives. Tetrahedron: Asymmetry, 1998, 9, 745-748.
65. Thomas, A. A.; Sharpless, K. B. The catalytic asymmetric aminohydroxylation of unsaturated phosphonates. J. Org. Chem., 1999, 64, 8379-8385.
66. Mandal, T.; Samanta, S.; Zhao, C.-G. Organocatalytic highly enantioselective nitroaldol reaction of α -ketophosphonates and nitromethane. Org. Lett., 2007, 9, 943-945.
67. For selected reviews, see: a) Enders, D.; Shilvock, J. P. Some recent applications of α -amino nitrile chemistry. Chem. Soc. Rev., 2000, 29, 359-373.
68. Gröger, H. Catalytic enantioselective Strecker reactions and analogous syntheses. Chem. Rev., 2003, 103, 2795-2828.
69. Taylor, M. S.; Jacobsen, E. N. Asymmetric catalysis by chiral hydrogen-bond donors. Angew. Chem., Int. Ed., 2006, 45, 1520-1543.
70. Merino, P.; Marqués-López, E.; Tejero, T.; Herrera, R. P. Organocatalyzed Strecker reactions. Tetrahedron, 2009, 65, 1219-1234.
71. Reingruber, R.; Baumann, T.; Dahmen, S.; Bräse, S. Use of the chiral pool-practical asymmetric organocatalytic Strecker reaction with quinine. Adv. Synth. Catal., 2009, 351, 1019-1024.
72. Momiyama, N.; Yamamoto, H. Catalytic enantioselective synthesis of α - aminooxy and α -hydroxy ketone using nitrosobenzene. J. Am. Chem. Soc. 2003, 125, 6038-6039.
73. For selected examples, see: a) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. The direct and enantioselective organocatalytic α - oxidation of aldehydes. J. Am. Chem. Soc., 2003, 125, 10808-10809.
74. Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Direct proline catalysed asymmetric α -aminooxylation of aldehydes. Tetrahedron Lett., 2003, 44, 8293-8296.
75. Bøgevig, A.; Sundén, H.; Córdova, A. Direct catalytic enantioselective α -aminoxylation of ketones: a stereoselective synthesis of α - hydroxy and α, α'-dihydroxy ketones. Angew. Chem., Int. Ed., 2004, 43, 1109-1112.
76. 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.
77. Guo, H.-M.; Cheng, L.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. L-Prolinamide-catalysed direct nitroso aldol reactions of α -branched aldehydes: a distinct regioselectivity from that with L-proline. Chem. Commun., 2006, 429-431.
78. Kano, T.; Ueda, M.; Takai, J.; Maruoka, K. Direct asymmetric hydroxyamination reaction catalysed by an axially chiral secondary amine catalyst. J. Am. Chem. Soc., 2006, 128, 6046-6047.
79. López-Cantarero, J.; Cid, M. B.; Poulsen, T. B.; Bella, M.; García Ruano, J. L.; Jørgensen, K. A. Intriguing behavior of cinchona alkaloids in the enantioselective organocatalytic hydroxyamination of α -substituted- α -cyanoacetates. J. Org. Chem., 2007, 72, 7062-7065.
80. For reviews, see: a) Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Stereoselective cyclopropanation reactions. Chem. Rev., 2003, 103, 977-1050.
81. Aziridines and Epoxides in Organic Synthesis, (Ed.: Yudin, A. K.), Wiley-VCH, Weinheim, 2006.
82. Pellissier, H. Recent developments in asymmetric cyclopropanation. Tetrahedron, 2008, 64, 7041-7095.
83. a) Faust, R. Fascinating natural and artificial cyclopropane architectures. Angew. Chem., Int. Ed., 2001, 40, 2251-2253.
84. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Biosynthesis and metabolism of cyclopropane rings in natural compounds. Chem. Rev., 2003, 103, 1625-1648.
85. a) Cativiela, C.; Diaz-de-Villegas, M. D. Stereoselective synthesis of quaternary α-amino acids. Part 2: cyclic compounds. Tetrahedron: Asymmetry, 2000, 11, 645-732.
86. Donaldson, W. A. Synthesis of cyclopropane containing natural products. Tetrahedron, 2001, 57, 8589-8627.
87. Reissig, H.-U.; Zimmer, R. Donor - acceptor-substituted cyclopropane derivatives and their application in organic synthesis. Chem. Rev., 2003, 103, 1151-1196.
88. For selected examples, see: a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. New chiral ruthenium bis(oxazolinyl)pyridine catalyst. Efficient asymmetric cyclopropanation of olefins with diazoacetates. J. Am. Chem. Soc., 1994, 116, 2223-2224.
89. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalysed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid. J. Am. Chem. Soc., 1996, 118, 6897-6907.
90. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Application of chiral sulfides to catalytic asymmetric aziridination and cyclopropanation with in situ generation of the diazo compound. Angew. Chem., Int. Ed., 2001, 40, 1433-1436.
91. Zhu, S.; Perman, J. A.; Zhang, X. P. Acceptor/acceptor-substituted diazo reagents for carbene transfers: cobalt-catalysed asymmetric Z-cyclopropanation of alkenes with α -nitrodiazoacetates. Angew. Chem., Int. Ed., 2008, 47, 8460-8463.
92. a) Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Organic-catalyst-mediated cyclopropanation reaction. Angew. Chem., Int. Ed., 2003, 42, 828-831.
93. Bremeyer, N.; Smith, S. C.; Ley, S. V.; Gaunt, M. J. An intramolecular organocatalytic cyclopropanation reaction. Angew. Chem., Int. Ed., 2004, 43, 2681-2684.
94. Kojima, S.; Suzuki, M.; Watanabe, A.; Ohkata, K. Asymmetric synthesis of activated cyclopropanes catalysed by cinchonidine as a chiral Brønsted base. Tetrahedron Lett., 2006, 47, 9061-9065.
95. McCooey, S. H.; McCabe, T.; Connon, S. J. Stereoselective synthesis of highly functionalized nitrocyclopropanes via organocatalyic conjugate addition to nitroalkenes. J. Org. Chem., 2006, 71, 7494-7497.
96. Xuan, Y.-n.; Nie, S.-z.; Dong, L.-t.; Zhang, J.-m.; Yan, M. Highly enantioselective synthesis of nitrocyclopropanes via organocatalytic conjugate addition of bromomalonate to α, β-unsaturated nitroalkenes. Org. Lett., 2009, 11, 1583-1586.
97. Russo, A.; Lattanzi, A. Stereoselective synthesis of functionalised cyclopropanes from nitroalkenes via an organocatalysed Michael-initiated ringclosure approach. Tetrahedron: Asymmetry, 2010, 21, 1155-1157.
98. Lattanzi, A. Enantioselective Michael addition of malonate esters to nitroolefins organocatalysed by diaryl-2-pyrrolidinemethanols. Tetrahedron: Asymmetry, 2006, 17, 837-841.
99. Mature, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Turner Jones, E. T. T., Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. A practical enantioselective synthesis of α, α -diaryl-2- pyrrolidinemethanol. Preparation and chemistry of the corresponding oxazaborolidines. J. Org. Chem., 1991, 56, 751-762.
100. a) Porter, M. J.; Skidmore, J. Asymmetric epoxidation of electron-deficient olefins. Chem. Commun., 2000, 1215-1225.
101. Lattanzi, A. Advances in asymmetric epoxidation of α, β-unsaturated carbonyl compounds: the organocatalytic approach. Curr. Org. Synth., 2008, 5, 117-133.
102. Díez, D.; Núñez, M. G.; Antón, A. B.; García, P.; Moro, R. F.; Garrido, N.M.; Marcos, I. S.; Basabe, P.; Urones, J. G. Asymmetric epoxidation of electron-deficient olefins. Curr. Org. Synth., 2008, 5, 186-216.
103. Lattanzi, A. In Catalytic Asymmetric Conjugate Reactions, (Ed. Córdova, A.), Wiley-VCH, Weinheim, 2010, p. 351-392.
104. Lauret, C. Epoxy ketones as versatile building blocks in organic synthesis. Tetrahedron: Asymmetry, 2001, 12, 2359-2383.
105. Kakei, H.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Catalytic asymmetric epoxidation of α, β -unsaturated esters using an yttrium-biphenyldiol complex. J. Am. Chem. Soc., 2005, 127, 8962-8963.
106. For selected examples, see: a) Marigo, M.; Franzén, G.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. Asymmetric organocatalytic epoxidation of α, β -unsaturated aldehydes with hydrogen peroxide. J. Am. Chem. Soc., 2005, 127, 6964-6965.
107. Zhao, G. L.; Ibrahem, I.; Sundén, H.; Córdova, A. Amine-catalysed asymmetric epoxidation of α, β -unsaturated aldehydes. Adv. Synth. Catal., 2007, 349, 1210-1224.
108. Wang, X.; Reisinger, C. M.; List, B. Catalytic asymmetric epoxidation of cyclic enones. J. Am. Chem. Soc., 2008, 130, 6070-6071.
109. Lattanzi, A. Enantioselective epoxidation of α, β -enones promoted by α, α - diphenyl-L-prolinol as bifunctional organocatalyst. Org. Lett., 2005, 7, 2579-2582.
110. Lattanzi, A. Bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol: an improved organocatalyst for the asymmetric epoxidation of α, β -enones. Adv. Synth. Catal., 2006, 348, 339-346.
111. Lattanzi, A.; Russo, A. Diaryl-2-pyrrolidinemethanols catalysed enantioselective epoxidation of α, β -enones: new insight into the effect of structural modification of the catalyst on reaction efficiency. Tetrahedron, 2006, 62, 12264-12269.
112. Russo, A.; Lattanzi, A. Asymmetric epoxidation of trans-chalcones organocatalysed by β -amino alcohols. Eur. J. Org. Chem., 2008, 2767-2773.
113. Li, Y.; Liu, X.; Yang, Y.; Zhao, G. 4-Substituted- α, α -diaryl-prolinols improve the enantioselective catalytic epoxidation of α, β -enones. J. Org. Chem., 2007, 72, 288-291.
114. Cui, H.; Li, Y.; Zheng, C.; Zhao, G.; Zhu, S. Enantioselective catalytic epoxidation of α, β -enones promoted by fluorous α, α -diaryl-L-prolinols. J. Fluor. Chem., 2008, 129, 45-50.
115. Lu, J.; Xu, Y.-H.; Liu, F.; Loh, T.-P. Enantioselective epoxidation of α, β - enones promoted by (1R,3S,4S)-2-azanorbornyl-3-methanol as an organocatalyst. Tetrahedron Lett., 2008, 49, 6007-6008.
116. Zheng, C.; Li, Y.; Yang, Y.; Wang, H. f.; Cui, H.; Zhang, J.; Zhao, G. Highly efficient asymmetric epoxidation of electron-deficient α, β -enones and related applications to organic synthesis. Adv. Synth. Catal., 2009, 351, 1685-1691.
117. Huang, D.; Huang, L. Asymmetric synthesis of (-)-dehydroclausenamide. Tetrahedron, 1990, 46, 3135-3142.
118. a) Juliá, S.; Masana, J.; Vega, J. C. Synthetic enzymes. Highly stereoselective epoxidation of chalcone in a triphasic toluene-water-poly[(S)-alanine] system. Angew. Chem., Int. Ed., 1980, 19, 929-930.
119. Juliá, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annunziata, R.; Molinari, H. Synthetic enzymes. Part 2. Catalytic asymmetric epoxidation by means of polyaminoacids in a triphase system. J. Chem. Soc., Perkin Trans. 1, 1982, 1317-1324.
120. Sun, B.-F.; Hong, R.; Kang, Y.-B.; Deng, L. Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins. J. Am. Chem. Soc., 2009, 131, 10384-10385.
121. Russo, A.; Lattanzi, A. Asymmetric epoxidation of 2-arylidene-1,3- diketones: facile access to synthetically useful epoxides. Org. Biomol. Chem., 2010, 8, 2633-2638.
122. Goudreau, N.; Cameron, D. R.; Déziel, R.; Haché, B.; Jakalian, A.; Malenfant, E.; Naud, J.; Ogilvie, W. W.; O'Meara, J.; White, P. W.; Yoakim, C. Optimization and determination of the absolute configuration of a series of potent inhibitors of human papillomavirus type-11 E1-E2 protein-protein interaction: A combined medicinal chemistry, NMR and computational chemistry approach. Bioorg. Med. Chem., 2007, 15, 2690-2700.
123. For recent reviews on organocatalytic asymmetric conjugate additions: a) Vicario, J. L.; Badía, D.; Carrillo, L. Organocatalytic enantioselective Michael and hetero-Michael reactions. Synthesis, 2007, 2065-2092.
124. Almaşi, D.; Alonso, D. A.; Nájera, C. Organocatalytic asymmetric conjugate additions. Tetrahedron: Asymmetry, 2007, 18, 299-365.
125. Tsogoeva, S. B. Recent advances in asymmetric organocatalytic 1,4-conjugate additions. Eur. J. Org. Chem., 2007, 1701-1716.
126. Catalytic Asymmetric Conjugate Reactions, (Ed. Córdova, A.), Wiley-VCH, Weinheim, 2010.
127. a) Wynberg, H.; Helder, R. Asymmetric induction in the alkaloid-catalysed Michael reaction. Tetrahedron Lett., 1975, 10, 4057-4060.
128. Hermann, K.; Wynberg, H. Asymmetric induction in the Michael reaction. J. Org. Chem., 1979, 44, 2238-2244.
129. Trost, B. M.; Shuey, C. D.; Di Ninno, F.; McElvain, S. S. A stereocontrolled total synthesis of (±)-hirsutic acid C. J. Am. Chem. Soc., 1979, 101, 1284-1285.
130. Helder, R.; Arends, R.; Bolt, W.; Hiemstra, H.; Wynberg, H. Alkaloid catalysed asymmetric synthesis. III. The addition of mercaptans to 2-cyclohexene-1-one; determination of enantiomeric excess using carbon-13 NMR. Tetrahedron Lett., 1977, 12, 2181-2182.
131. a) Pracejus, H.; Wilcke, F.-W.; Hanemann, K. Asymmetrically catalysed additions of thiols to derivatives of α -aminoacrylic acid and nitroolefins. J. Prakt. Chem., 1977, 319, 219-229.
132. Yamashita, H.; Mukaiyama, T. Asymmetric Michael addition of thiophenol to maleic acid esters. Chem. Lett., 1985, 363-366.
133. Matsumoto, K.; Uchida, T. Molecular and reaction design based on high-pressure organic reactions. 5. Asymmetric induction under high-pressure. Michael addition of nitromethane to chalcone catalysed by chiral alkaloids. Chem. Lett., 1981, 1673-1676.
134. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H. High-pressure asymmetric Michael additions of thiols, nitromethane, and methyl oxoindancarboxylate to enones. J. Org. Chem., 1988, 53, 1157-1161.
135. Kobayashi, N.; Iwai, K. Asymmetric addition of thioglycolic acid to nitro olefins catalysed by cinchona alkaloids. J. Org. Chem., 1981, 46, 1823-1828.
136. Latvala, A.; Stanchev, S.; Linden, A.; Hesse, M. Unexpected change of absolute configuration in asymmetric Michael addition of methyl vinyl ketone to 2-nitrocycloalkanones. Tetrahedron: Asymmetry, 1993, 4, 173-176.
137. Ahuja, R. R.; Natu, A. A.; Gogte, V. N. Optical induction. IV. Optical induction by using homogeneous catalysts. Tetrahedron Lett., 1980, 21, 4743-4744.
138. Kumar, A.; Salunkhe, R. V.; Rane, R. A.; Dike, S. Y. Novel catalytic enantioselective protonation (proton transfer) in Michael addition of benzenethiol to α -arylacrylates: synthesis of (S)- naproxen and α -arylpropionic acids or esters. J. Chem. Soc., Chem. Commun., 1991, 485-486.
139. a) Kobayashi, N.; Iwai, K. Functional polymers. 1. Poly(cinchona alkaloidco-acrylonitrile)s. New polymer catalysts for asymmetric synthesis. J. Am. Chem. Soc., 1978, 100, 7071-7072.
140. Kobayashi, N.; Iwai, K. Functional polymers. 9. Asymmetric catalysis by new cinchona alkaloid derivatives. Effect of C(3) substituent on asymmetric induction. J. Polym. Sci. Polym. Chem. Ed., 1982, 20, 85-90.
141. Inagaki, M.; Hiratake, J.; Yamamoto, Y.; Oda, J. Asymmetric induction in the base-catalysed reactions using polymersupported quinines with spacer groups. Bull. Chem. Soc. Jpn., 1987, 60, 4121-4126.
142. Alvarez, R.; Hourdin, M.-A.; Cavé, C.; d'Angelo, J.; Chaminade, P. New polymer-supported catalysts derived from cinchona alkaloids: their use in the asymmetric Michael reaction. Tetrahedron Lett., 1999, 40, 7091-7094.
143. a) Kobayashi, N.; Iwai, K. Functional polymers. 6. Unusual catalysis of polymeric Cinchona alkaloids in asymmetric reaction. Tetrahedron Lett., 1980, 21, 2167-2170.
144. Hodge, P.; Khoshdel, E.; Waterhouse, J.; Fréchet, J. M. J. Michael additions catalysed by Cinchona alkaloids bound via their vinyl groups to preformed crosslinked polymers. J. Chem. Soc., Perkin Trans. 1, 1985, 2327-2331.
145. T. Asymmetric synthesis based on chiral diamines having a pyrrolidine ring. Tetrahedron, 1981, 37, 4111-4119.
146. Mukaiyama, T.; Ikegawa, A.; Suzuki, K. Highly enantioselective Michael addition of thiols to 2- cyclohexenone by using (2S,4S)-2-(anilinomethyl)-1-ethyl-4- hydroxypyrrolidine as a chiral catalyst. Chem. Lett., 1981, 165-168.
147. Szöllösi, G.; Bartók, M. Enantioselective Michael addition catalysed by cinchona alkaloids. Chirality, 2001, 13, 614-618.
148. Szöllösi, G.; Forgó, P.; Bartók, M. Hydrogenation of cinchona alkaloids over supported Pt catalyst. Chirality, 2003, 15, S82-S89.
149. Bonfils, F.; Cazaux, I.; Hodge, P.; Caze, C. Michael reactions carried out using a bench-top flow system. Org. Biomol. Chem., 2006, 4, 493-497.
150. Li, H.; Wang, Y.; Tang, L.; Deng, L. Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. J. Am. Chem. Soc., 2004, 126, 9906-9907.
151. Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition. Angew. Chem., Int. Ed., 2005, 44, 105-108.
152. Li, H.; Song, J.; Liu, X.; Deng, L. Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones. J. Am. Chem. Soc., 2005, 127, 8948-8949.
153. Wu, F.; Li, H.; Hong, R.; Deng, L. Construction of quaternary stereocenters by efficient and practical conjugate additions to α, β -unsaturated ketones with a chiral organic catalyst. Angew. Chem., Int. Ed., 2006, 45, 947-950.
154. Wu, F.; Hong, R.; Khan, J.; Liu, X.; Deng, L. Asymmetric synthesis of chiral aldehydes by conjugate additions with bifunctional organocatalysis by cinchona alkaloids. Angew. Chem., Int. Ed., 2006, 45, 4301-4305.
155. Wang, Y.; Liu, X.; Deng, L. Dual-function cinchona alkaloid catalysis: catalytic asymmetric tandem conjugate addition-protonation for the direct creation of nonadjacent stereocenters. J. Am. Chem. Soc., 2006, 128, 3928-3930.
156. Fringuelli, F.; Castrica, L.; Pizzo, F.; Vaccaro, L. Enantioselective Michael addition of dimethyl malonate to (E)- β -nitrostyrenes catalysed by cinchona alkaloids under solvent-free condition. Lett. Org. Chem., 2008, 5, 602-606.
157. Chen, F.-X; Shao, C.; Wang, Q.; Gong, P.; Zhang, D.-Y.; Zhang, B.-Z.; Wang, R. An enantioselective Michael addition of malonate to nitroalkenes catalysed by low loading demethylquinine salts in water. Tetrahedron Lett., 2007, 48, 8456-8459.
158. Brandes, S.; Niess, B.; Bella, M.; Prieto, A.; Overgaard, J.; Jørgensen, K. A. Non-biaryl atropisomers in organocatalysis. Chem. Eur. J., 2006, 12, 6039-6052.
159. Ooi, T.; Miki, T.; Taniguchi, M.; Shiraishi, M.; Takeuchi, M.; Maruoka, K. Highly enantioselective construction of quaternary stereocenters on β -keto esters by phase-transfer catalytic asymmetric alkylation and Michael reaction. Angew. Chem., Int. Ed., 2003, 42, 3796-3798.
160. Wang, L.; Li, H.; Zu, L.; Jiang, W.; Wang, W. Organocatalytic, enantioselective conjugate addition of nitroalkanes to nitroolefins. Adv. Synth. Catal., 2006, 348, 2047-2050.
161. 2-symmetric tridentate bis(oxazoline) and bis(thiazoline) zinc complexes. J. Am. Chem. Soc., 2006, 128, 7418-7419.
162. Alcántara, M. D.; Escribano, F. C.; Gómez-Sánchez, A.; Diánez, M. J.; Estrada, M. D.; López-Castro, A.; Pérez-Garrido, S. Synthesis of aliphatic 1,3-dinitro compounds. Synthesis, 1996, 64-70.
163. Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A. One-pot synthesis of 1,3-dinitroalkanes under heterogeneous catalysis. Synthesis, 2004, 1938-1940.
164. Gogoi, S.; Zhao, C.-G. Organocatalysed enantioselective synthesis of 6- amino-5-cyanodihydropyrano[2,3-c]pyrazoles. Tetrahedron Lett., 2009, 50, 2252-2255.
165. Bartoli, G.; Bosco, M.; Carlone, A.; Cavalli, A.; Locatelli, M.; Mazzanti, A.; Ricci, P.; Sambri, L.; Melchiorre, P. Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides. Angew. Chem., Int. Ed., 2006, 45, 4966-4970.
166. Capuzzi, M.; Perdicchia, D.; Jørgensen, K. A. Highly enantioselective approach to geminal bisphosphonates by organocatalysed Michael-type addition of β -ketoesters. Chem. Eur. J., 2008, 14, 128-135.
167. a) Zhang, S.; Gangal, G.; Uludaǧ, H. 'Magic bullets' for bone diseases: progress in rational design of bone-seeking medicinal agents. Chem. Soc. Rev. 2007, 36, 507-531.
168. Kotsikorou, E.; Song, Y.; Chan, J. M. W.; Faelens, S.; Tovian, Z.; Broderick, E.; Bakalara, N.; Docampo, R.; Olfield, E. Bisphosphonate Inhibition of the Exopolyphosphatase Activity of the Trypanosoma brucei Soluble Vacuolar Pyrophosphatase. J. Med. Chem. 2005, 48, 6128-6139, and references therein.
169. Wang, H.-F.; Zheng, C.-W.; Yang, Y.-Q.; Chai, Z.; Zhao, G. An unexpected tandem enantioselective Michael addition/oxa-nucleophilic rearrangement reaction of β, γ-unsaturated α -keto esters catalysed by cinchona alkaloids. Tetrahedron: Asymmetry, 2008, 19, 2608-2615.
170. Cid, B.; López-Cantarero, J.; Duce, S.; García Ruano, J. L. Enantioselective organocatalytic approach to the synthesis of α, α -disubstituted cyanosulfones. J. Org. Chem., 2009, 74, 431-434.
171. Alemán, J.; Richter, B.; Jørgensen, K. A. Organocatalytic highly enantioselective α -arylation of β -ketoesters. Angew. Chem., Int. Ed., 2007, 46, 5515-5519.
172. Russo, A.; Perfetto, A.; Lattanzi, A. Back to natural cinchona alkaloids: highly enantioselective Michael addition of malononitrile to enones. Adv. Synth. Catal., 2009, 351, 3067-3071.
173. For a review, see: Cui, H.; Chen, Y. α, α -Dicyanoalkenes: versatile vinylogous nucleophiles for organic synthesis. Chem. Commun., 2009, 4479-4486.
174. Xue, D.; Chen, Y.-C.; Wang, Q.-W.; Cun, L.-F.; Zhu, J.; Deng, J.-G. Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalysed by modified cinchona alkaloids. Org. Lett., 2005, 7, 5293-5296.
175. Poulsen, T. B.; Bell, M.; Jørgensen, K. A. Organocatalytic asymmetric allylic carbon-carbon bond formation. Org. Biomol. Chem., 2006, 4, 63-70.
176. Bell, M.; Frisch, K.; Jørgensen, K. A. Organocatalytic asymmetric deconjugative Michael additions. J. Org. Chem., 2006, 71, 5407-5410.
177. For a comprehensive review on the sulfa-Michael reaction, see: Enders, D.; Lüttgen, K; Narine, A. A. Asymmetric sulfa-Michael additions. Synthesis, 2007, 959-980.
178. For a recent review on the organocatalytic aza-Michael reaction, see: Enders, D.; Wang, C.; Liebich, J. X. Organocatalytic asymmetric aza-Michael additions. Chem. Eur. J., 2009, 15, 11058-11076.
179. For a comprehensive review on the phospha-Michael reaction, see: Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. The phospha-Michael addition in organic synthesis. Eur. J. Org. Chem., 2006, 29-49.
180. McDaid, P.; Chen, Y.; Deng, L. A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst. Angew. Chem., Int. Ed., 2002, 41, 338-340.
181. Skarzewski, J.; Zielińska-Błajet, M.; Turowska-Tyrk, I. Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks. Tetrahedron: Asymmetry, 2001, 12, 1923-1928.
182. Zielińska-Błajet, M.; Kowalczyk, R.; Skarzewski, J. Ring-closure reactions through intramolecular substitution of thiophenoxide by oxygen and nitrogen nucleophiles: simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles. Tetrahedron, 2005, 61, 5235-5240.
183. Athawale, V.; Manjrekar, N. Mild chemo-enzymatic synthesis of polymersupported cinchona alkaloids and their application in asymmetric Michael addition. Tetrahedron Lett., 2001, 42, 4541-4543.
184. Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Immobilization of catalysts derived from cinchona alkaloids on modified poly(ethylene glycol). Tetrahedron: Asymmetry, 2003, 14, 461-467.
185. Dodda, R.; Goldman, J. J.; Mandal, T.; Zhao, C.-G; Broker, G. A.; Tiekink, E. R. T. Synthesis of 2,3,4-trisubstituted thiochromanes using an organocatalytic enantioselective tandem Michael-Henry reaction. Adv. Synth. Catal., 2008, 350, 537-541.
186. Sekino, E.; Kumamoto, T.; Tanaka, T.; Ikeda, T.; Ishikawa, T. Concise synthesis of anti-HIV-1 active (+)-inophyllum B and (+)-calanolide A by application of (-)-quinine catalysed intramolecular oxo-Michael addition. J. Org. Chem., 2004, 69, 2760-2767.
187. Merschaert, A.; Delbeke, P.; Daloze, D.; Dive, G. The rational design of modified cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes. Tetrahedron Lett., 2004, 45, 4697-4701.
188. Dittmer, C.; Raabe, G.; Hintermann, L. Asymmetric Cyclization of 2'- hydroxychalcones to flavanones: catalysis by chiral Brønsted acids and bases. Eur. J. Org. Chem., 2007, 5886-5898.
189. Russo, A.; Lattanzi, A. Catalytic asymmetric β-peroxidation of nitroalkenes. Adv. Synth. Catal., 2008, 350, 1991-1995.
190. Wang, J.; Li, H.; Zu, L.; Wang, W. Enantioselective organocatalytic Michael addition reactions between N-heterocycles and nitroolefins. Org. Lett., 2006, 7, 1391-1394.
191. Perdicchia, D.; Jørgensen, K. A. Asymmetric aza-Michael reactions catalysed by cinchona alkaloids. J. Org. Chem., 2007, 72, 3565-3568.
192. Scettri, A.; Massa, A.; Palombi, L.; Villano, R.; Acocella, M. R. Organocatalytic asymmetric aza-Michael addition of aniline to chalcones under solventfree conditions. Tetrahedron: Asymmetry, 2008, 19, 2149-2152.
193. Wang, J.; Heikkinen, L. D.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Wang, W. Quinine-catalysed enantioselective Michael addition of diphenyl phosphite to nitroolefins: synthesis of chiral precursors of α-substituted β-aminophosphonates. Adv. Synth. Catal., 2007, 349, 1052-1056.
194. Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mazzanti, A.; Sambri L.; Melchiorre, P. Organocatalytic asymmetric hydrophosphination of nitroalkenes. Chem. Commun., 2007, 722-724.
195. For reviews on α -heterofunctionalization of carbonyl compounds, see: a) Marigo, M.; Jørgensen, K. A. Organocatalytic direct asymmetric α - heteroatom functionalization of aldehydes and ketones. Chem. Commun., 2006, 2001-2011.
196. Guillena, G.; Ramón, D. J. Enantioselective α - heterofunctionalisation of carbonyl compounds: organocatalysis is the simplest approach. Tetrahedron: Asymmetry, 2006, 17, 1465-1492.
197. For selected reviews on the asymmetric α -amination of carbonyl compounds, see: a) Greck, C.; Drouillat, B.; Thomassigny, C. Asymmetric electrophilic α -amination of carbonyl groups. Eur. J. Org. Chem., 2004, 1377-1385.
198. Janey, J. M. Recent advances in catalytic, enantioselective α -aminations and α -oxygenations of carbonyl compounds. Angew. Chem., Int. Ed., 2005, 44, 4292-4300.
199. Duthaler, R. O. Proline-catalysed asymmetric α -amination of aldehydes and ketones - An astonishingly simple access to optically active α - hydrazino carbonyl compounds. Angew. Chem., Int. Ed., 2003, 421, 975-978.
200. Nair, V.; Biju, A. T.; Mathew, S. C.; Babu, B. P. Carbon-nitrogen bondforming reactions of dialkyl azodicarboxylate: a promising synthetic strategy. Chem. Asian J., 2008, 3, 810-820.
201. Pihko, P. M.; Pohjakallio, A. Enantioselective organocatalytic Diels aminations: α -aminations of cyclic β-keto esters and β -keto lactones with cinchonidine and cinchonine. Synlett, 2004, 2115-2118.
202. a) Plietker, B. New oxidative pathways for the synthesis of β -hydroxy ketones- the α -hydroxylation and ketohydroxylation. Tetrahedron: Asymmetry, 2005, 16, 3453-3459.
203. Christoffers, J.; Baro, A.; Werner, T. α - Hydroxylation of β -dicarbonyl compounds. Adv. Synth. Catal., 2004, 346, 143-151.
204. Merino, P.; Tejero, T. Organocatalysed asymmetric α - aminoxylation of aldehydes and ketones-An efficient access to enantiomerically pure α -hydroxycarbonyl compounds, diols, and even amino alcohols. Angew. Chem., Int. Ed., 2004, 43, 2995-2997.
205. For an overview of synthetic methods to indoxacarb, see: McCann, S. F.; Annis, G. D.; Shapiro, R.; Piotrowski, D. W.; Lahm, G. P.; Long, J. K.; Lee, K. C.; Hughes, M. M.; Myers, B. J.; Griswold, S. M.; Reeves, B. M.; March, R. W.; Sharpe, P. L.; Lower, P.; Barnette, W. E.; Wing, K. D. The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides. Pest. Manag. Sci., 2001, 57, 153-164.
206. Acocella, M. R.; García Mancheño, O.; Bella, M.; Jørgensen, K. A. Organocatalytic asymmetric hydroxylation of β -keto esters: metal-free synthesis of optically active anti-diols. J. Org. Chem., 2004, 69, 8165-8167.
207. Sobhani, S.; Fielenbach, S. D.; Marigo, M.; Wabnitz, T. C. Jørgensen, K. A. Direct Organocatalytic asymmetric α -sulfenylation of activated C-H bonds in lactones, lactams, and β -dicarbonyl compounds. Chem. Eur. J., 2005, 11, 5689-5694.
208. Fang, L.; Lin, A.; Hu, H.; Zhu, C. Highly enantioselective sulfenylation of β- ketoesters: H-bond acceptor catalysis. Chem. Eur. J., 2009, 15, 7039-7043.
209. Polaske, N. W.; Dubey, R.; Nichol, G. S.; Olenyuk, B. Enantioselective organocatalytic α -sulfenylation of substituted diketopiperazines. Tetrahedron: Asymmetry, 2009, 20, 2742-2750.
210. For reviews, see: a) Poulsen, T. B.; Jørgensen, K. A. Catalytic asymmetric Friedel-Crafts alkylation reactions copper showed the way. Chem. Rev., 2008, 108, 2903-2915.
211. You, S.-L.; Cai, Q.; Zeng, M. Chiral Brønsted acid catalysed Friedel-Crafts alkylation reactions. Chem. Soc. Rev., 2009, 38, 2190-2201.
212. Marqués-López, E.; Diez-Martinez, A.; Merino, P.; Herrera, R. P. The Role of the indole in important organocatalytic enantioselective Friedel-Crafts alkylation reactions, Curr. Org. Chem. 2009, 13, 1585-1609.
213. Catalytic Asymmetric Friedel-Crafts Alkylations, (Eds. Bandini, M. Umani-Ronchi, A.), Wiley-VCH, Weinheim, 2009.
214. Terrasson, V.; de Figuereido, R. M.; Campagne, J. M. Organocatalyzed asymmetric Friedel- Crafts reactions. Eur. J. Org. Chem., 2010, 2635-2655.
215. Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yan, P.; Surya Prakash, G. K. Highly Enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate. Angew. Chem., Int. Ed., 2005, 44, 3086-3089.
216. For recent reviews, see: a) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Enantioselective catalytic formation of quaternary stereogenic centers. Eur. J. Org. Chem., 2007, 5969-5994.
217. Bella, M.; Gasperi, T. Organocatalytic formation of quaternary stereocenters. Synthesis, 2009, 1583-1614.
218. Jautze, S., Peters, R. Catalytic asymmetric Michael additions of α -cyanoacetates. Synthesis, 2010, 365-388.
219. a) Peddibhotla, S. 3-Substituted-3-hydroxy-2-oxindole, an emerging new scaffold for drug discovery with potential anti-cancer and other biological activities. Curr. Bioact. Compd., 2009, 5, 20-38.
220. 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.
221. Marti, C.; Carreira, E. M. Construction of spiro[pyrrolidine-3,3'-oxindoles] - recent applications to the synthesis of oxindole alkaloids. Eur. J. Org. Chem., 2003, 2209-2219.
222. Deng, J.; Zhang, S.; Ding, P.; Jiang, H.; Wang, W.; Li, J. Facile creation of 3-indolyl-3-hydroxy-2-oxindoles by an organocatalytic enantioselective Friedel-Crafts reaction of indoles with isatins. Adv. Synth. Catal., 2010, 352, 833-838.
223. Brandes, S.; Bella, M.; Kjærsgaard, A.; Jørgensen, K. A. Chirally aminated 2-naphthols - organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination. Angew. Chem., Int. Ed., 2006, 45, 1147-1151.
224. For reviews, see: a) Kobayashi, S.; Ishitani, H. Catalytic enantioselective addition to imines. Chem. Rev., 1999, 99, 1069-1094.
225. Shibasaki, M.; Matsunaga, S. Design and application of linked-BINOL chiral ligands in bifunctional asymmetric catalysis. Chem. Soc. Rev., 2006, 35, 269-279.
226. For a review, see: Córdova, A. The direct catalytic asymmetric Mannich reaction. Acc. Chem. Res., 2004, 37, 102-112.
227. For reviews, see: a) Ting, A.; Schaus, S. E. Organocatalytic asymmetric Mannich reactions: new methodology, catalyst design, and synthetic applications. Eur. J. Org.Chem., 2007, 35, 5797-5815.
228. Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Organocatalysed asymmetric Mannich reactions. Chem. Soc. Rev., 2008, 37, 29-41.
229. Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. Asymmetric Mannich reactions of β -keto esters with acyl imines catalysed by cinchona alkaloids. J. Am. Chem. Soc., 2005, 127, 11256-11257.
230. Ting, A.; Lou, S.; Schaus, S. E. Highly diastereoselective asymmetric Mannich reactions of 1,3-dicarbonyls with acyl imines. Org. Lett., 2006, 8, 2003-2006.
231. Lou, S.; Dai, P.; Schaus, S. E. Asymmetric Mannich reaction of dicarbonyl compounds with α -amido sulfones catalysed by cinchona alkaloids and synthesis of chiral dihydropyrimidones. J. Org.Chem., 2007, 72, 9998-10008.
232. Riant, O.; Kagan, H. B. Asymmetric Diels-Alder reaction catalysed by chiral bases. Tetrahedron Lett., 1989, 30, 7403-7406.
233. For a recent review, see: Merino, P.; Marquéz-López, E.; Tejero, T.; Herrera, R. P. Enantioselective organocatalytic Diels-Alder reactions. Synthesis, 2010, 1-26.
234. 2-chiral pyrrolidines. J. Chem. Soc., Perkin Trans. 1, 2001, 1002-1006.
235. Fache, F.; Piva, O. New perfluoroalkylated cinchona derivatives: synthesis and use in base-catalysed Diels-Alder reactions. Tetrahedron Lett., 2001, 42, 5655-5657.
236. Hintermann, L.; Schmitz, M. Enantioselective synthesis of phospholenes via asymmetric organocatalytic alkene isomerization. Adv. Synth. Catal., 2008, 350, 1469-1473.
237. For reviews, see: a) Singh, G. S.; D'hooghe, M.; De Kimpe, N. Synthesis and reactivity of C-heteroatom-substituted aziridines. Chem. Rev. 2007, 107, 2080-2135.
238. Schneider, C. Catalytic, enantioselective ring opening of aziridines. Angew.Chem., Int. Ed., 2009, 48, 2082-2084.
239. Wang, Z.; Sun, X.; Ye, S.; Wang, W.; Wang, B.; Wu, J. Quinine-catalysed enantioselective desymmetrization of meso-aziridines with benzenethiols. Tetrahedron: Asymmetry, 2008, 19, 964-969.
240. Lattanzi, A.; Della Sala, G. Desymmetrization of meso-N-acylaziridines with benzenethiols promoted by α, α -diaryl-L-prolinols Eur. J. Org. Chem., 2009, 1845-1848.