Enantioselective organocatalytic reactions with isatin

Current Organic Chemistry

Volumn 17, Issue 18, 2013, Pages 1957-1985

  Flores, MariFe ^a   Peña, Javier ^a   García García, Pilar ^b   Garrido, Narciso M ^a   Díez, David ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b INSTITUTO DE TECNOLOGÍA QUÍMICA   (Spain)

Author keywords

Aldol; Asymmetric Catalysis; Friedel Crafts; Henry; Isatin; Morita Baylis Hillman; Organocatalysis

Indexed keywords

KETONES; RATE CONSTANTS;

ALDOL; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE; FRIEDEL-CRAFTS; HENRY; ISATIN; MORITA-BAYLIS-HILLMAN; ORGANOCATALYSIS; ORGANOCATALYSTS; ORGANOCATALYTIC;

CATALYSIS;

EID: 84881355908     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113179990092     Document Type: Review

References (200)

1. Yoshikawa, M.; Murakami, T.; Kishi, A.; Sakurama, T.; Matsuda, H.; Nomura, M.; Matsuda, H.; Kubo, M., Novel indole s, o-bisdesmoside, calanthoside, the precursor glycoside of tryptanthrin, indirubin, and isatin, with increasing skin blood flow promoting effects, from two Calanthe species (Orchidaceae). Chem. Pharm. Bull. 1998, 46 (5), 886-888.
2. Bergman, J.; Lindström, J.-O.; Tilstam, U., The structure and properties of some indolic constituents in Couroupita guianensis Aubl. Tetrahedron 1985, 41 (14), 2879-2881.
3. Sumpter, W. C., The chemistry of isatin. Chem. Rev. 1944, 34 (3), 393-434.
4. Antonchick, A. P.; Gerding-Reimers, C.; Catarinella, M.; Schürmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H., Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products. Nat. Chem. 2010, 2 (9), 735-740
5. Vintonyak, V. V.; Warburg, K.; Kruse, H.; Grimme, S.; Hübel, K.; Rauh, D.; Waldmann, H., Identification of thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of the mycobacterium tuberculosis protein tyrosine phosphatase B. Angew. Chem. Int. Ed. 2010, 49 (34), 5902-5905.
6. da Silva, J. F. M.; Garden, S. J.; Pinto, A. C., The chemistry of isatins: A review from 1975 to 1999. J. Brazil. Chem. Soc. 2001, 12 (3), 273-286
7. Kumar, A.; Chimni, S. S., Catalytic asymmetric synthesis of 3-hydroxyoxindole: A potentially bioactive molecule. RSC Adv. 2012, 2 (26), 9748-9762.
8. Lashgari, N.; Ziarani, G. M., Synthesis of heterocyclic compounds based on isatin through 1, 3-dipolar cycloaddition reactions. Arkivoc 2012, 277-320.
9. Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K., Strategies for the enantioselective synthesis of spirooxindoles. Org. Biomol. Chem. 2012, 10 (27), 5165-5181.
10. List, B.; Editor, Asymmetric organocatalysis. [in: Top. Curr. Chem., 2010; 291]. Springer GmbH: 2010; p 460 pp
11. Christmann, M.; Braese, S.; Editors, Asymmetric synthesis-the essentials. Wiley-VCH Verlag GmbH & Co. KGaA: 2008; p 355 pp.
12. Mukaiyama, T., The directed aldol reaction. Org. React. 1982, 28, 203-331
13. Mahrwald, R.; Editor, Modern aldol reactions, vol. 1: Enolates, organocatalysis, biocatalysis and natural product synthesis. Wiley-VCH Verlag GmbH & Co. KGaA: 2004; p 335 pp
14. Mahrwald, R.; Editor, Modern aldol reactions, volume 2: Metal catalysis. Wiley-VCH Verlag GmbH & Co. KGaA: 2004; p 351 pp.
15. List, B.; Lerner, R. A.; Barbas, C. F., Proline-catalyzed direct asymmetric aldol reactions. J. Am. Chem. Soc. 2000, 122 (10), 2395-2396.
16. List, B., Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents. Acc. Chem. Res. 2004, 37 (8), 548-557
17. Notz, W.; Tanaka, F.; Barbas, 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 (8), 580-591
18. List, B., Proline-catalyzed asymmetric reactions. Tetrahedron 2002, 58 (28), 5573-5590
19. Pellissier, H., Asymmetric organocatalysis. Tetrahedron 2007, 63 (38), 9267-9331.
20. Wurtz, C. A., J. Prakt. Chem 1872, 5, 457-464.
21. Tang, Y. Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X. Z., Maremycins C and D, new diketopiperazines, and maremycins E and F, novel polycyclic spiro-indole metabolites isolated from streptomyces sp. Eur. J. Org. Chem. 2001, (2), 261-267
22. Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S., TMC-95 A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei sacc. Tc 1093-taxonomy, production, isolation, and biological activities. J. Antibiot. 2000, 53 (2), 105-109
23. Labroo, R. B.; Cohen, L. A., Preparative separation of the diastereoisomers of dioxindolyl-L-alanine and assignment of stereochemistry at C-3. J. Org. Chem. 1990, 55 (16), 4901-4904
24. Hewawasam, P.; Meanwell, N. A., Discovery of a novel class of bk channel openers: Enantiospecific synthesis and bk channel opening activity of 3-(5-chloro-2-hydroxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2h-indol-2-one. Bioorg. Med. Chem. Lett. 1997, 7 (10), 1255-1260
25. Tokunaga, T.; Hume, W. E.; Umezome, T.; Okazaki, K.; Ueki, Y.; Kumagai, K.; Hourai, S.; Nagamine, J.; Seki, H.; Taiji, M.; Noguchi, H.; Nagata, R., Oxindole derivatives as orally active potent growth hormone secretagogues. J. Med. Chem. 2001, 44 (26), 4641-4649
26. Hewawasam, P.; Erway, M.; Moon, S. L.; Knipe, J.; Weiner, H.; Boissard, C. G.; Post-Munson, D. J.; Gao, Q.; Huang, S.; Gribkoff, V. K.; Meanwell, N. A., Synthesis and structure-activity relationships of 3-aryloxindoles: A new class of calcium-dependent, large conductance potassium (maxi-k) channel openers with neuroprotective properties. J. Med. Chem. 2002, 45 (7), 1487-1499.
27. Shintani, R.; Inoue, M.; Hayashi, T., Rhodium-catalyzed asymmetric addition of aryl-and alkenylboronic acids to isatins. Angew. Chem. Int. Ed. 2006, 45 (20), 3353-3356
28. Nakamura, T.; Shirokawa, S.; Hosokawa, S.; Nakazaki, A.; Kobayashi, S., Enantioselective total synthesis of convolutamydines b and e. Org. Lett. 2006, 8 (4), 677-679
29. Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J., Rhodium-catalyzed addition of arylboronic acids to isatins: An entry to diversity in 3-aryl-3-hydroxyoxindoles. Org. Lett. 2006, 8 (13), 2715-2718
30. 2Zn addition to ZZ-ketoesters. Angew. Chem. Int. Ed. 2003, 42 (44), 5489-5492
31. Trost, B. M.; Frederiksen, M. U., Palladium-catalyzed asymmetric allylation of prochiral nucleophiles: Synthesis of 3-allyl-3-aryl oxindoles. Angew. Chem. Int. Ed. 2005, 44 (2), 308-310
32. Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S., Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and hh-keto esters using DBFOX ligand. J. Am. Chem. Soc. 2006, 128 (51), 16488-16489
33. Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R., Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyladdition/cyclization reaction sequences. J. Org. Chem. 2006, 71 (6), 2346-2351.
34. Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., Amino acid catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions. J. Am. Chem. Soc. 2001, 123 (22), 5260-5267
35. Dalko, P. I.; Moisan, L., In the golden age of organocatalysis. Angew. Chem. Int. Ed. 2004, 43 (39), 5138-5175.
36. Chen, G.; Wang, Y.; He, H.; Gao, S.; Yang, X.; Hao, X., L-proline-catalyzed asymmetric aldol condensation of N-substituted isatins with acetone. Heterocycles 2006, 68 (11), 2327-2333. We have detected a mistake in the configuration assigned by the authors. See references 17 and 30 of this review.
37. Angelici, G.; Correa, R. J.; Garden, S. J.; Tomasini, C., Water influences the enantioselectivity in the proline or prolinamide-catalyzed aldol addition of acetone to isatins. Tetrahedron Lett. 2009, 50 (7), 814-817.
38. Brogan, A. P.; Dickerson, T. J.; Janda, K. D., Enamine-based aldol organocatalysis in water: Are they really "All wet"? Angew. Chem. Int. Ed. 2006, 45 (48), 8100-8102
39. Hayashi, Y., In water or in the presence of water? Angew. Chem. Int. Ed. 2006, 45 (48), 8103-8104
40. Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A., Water in organocatalytic processes: Debunking the myths. Angew. Chem. Int. Ed. 2007, 46 (21), 3798-3800
41. Wang, C.; Jiang, Y.; Zhang, X.-X.; Huang, Y.; Li, B.-g.; Zhang, G.-l., Rationally designed organocatalyst for direct asymmetric aldol reaction in the presence of water. Tetrahedron Lett. 2007, 48 (24), 4281-4285.
42. Kinsella, M.; Duggan, P. G.; Lennon, C. M., Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin. Tetrahedron: Asymm. 2011, 22 (13), 1423-1433.
43. Chimni, S. S.; Mahajan, D., Small organic molecule catalyzed enantioselective direct aldol reaction in water. Tetrahedron: Asymm. 2006, 17 (14), 2108-2119
44. Tang, Z.; Cun, L. F.; Cui, X.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z., Design of highly enantioselective organocatalysts based on molecular recognition. Org. Lett. 2006, 8 (7), 1263-1266
45. García-Tellado, F.; Goswami, S.; Chang, S. K.; Geib, S. J.; Hamilton, A. D., Molecular recognition-a remarkably simple receptor for the selective complexation of dicarboxylic acids. J. Am. Chem. Soc. 1990, 112 (20), 7393-7394
46. Geib, S. J.; Vicent, C.; Fan, E.; Hamilton, A. D., A self-assembling, hydrogen-bonded helix. Angew. Chem. Int. Ed. 1993, 32 (1), 119-121.
47. Fu, S.-d.; Fu, X.-K.; Zhang, S.-P.; Zou, X.-C.; Wu, X.-J., Highly diastereoand enantioselective direct aldol reactions by 4-tert-butyldimethylsiloxysubstituted organocatalysts derived from N-prolylsulfonamides in water. Tetrahedron: Asymm. 2009, 20 (20), 2390-2396.
48. Chen, J.-R.; Liu, X.-P.; Zhu, X.-Y.; Li, L.; Qiao, Y.-F.; Zhang, J.-M.; Xiao, W.-J., Organocatalytic asymmetric aldol reaction of ketones with isatins: Straightforward stereoselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones. Tetrahedron 2007, 63 (42), 10437-10444.
49. Chen, J. R.; Lu, H. H.; Li, X. Y.; Cheng, L.; Wan, J.; Xiao, W. J., Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions. Org. Lett. 2005, 7 (20), 4543-4545
50. Cao, Y.-J.; Lu, H.-H.; Lai, Y.-Y.; Lu, L.-Q.; Xiao, W.-J., An effective bifunctional thiourea catalyst for highly enantio-and diastereoselective Michael addition of cyclohexanone to nitroolefins. Synthesis 2006, (22), 3795-3800
51. Notz, W.; List, B., Catalytic asymmetric synthesis of anti-1,2-diols. J. Am. Chem. Soc. 2000, 122 (30), 7386-7387
52. Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C., Enantioselective organocatalytic direct aldol reactions of dd-oxyaldehydes: Step one in a two-step synthesis of carbohydrates. Angew. Chem. Int. Ed. 2004, 43 (16), 2152-2154
53. Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G., Enantioselective direct aldol reaction "On water" Promoted by chiral organic catalysts. Org. Lett. 2007, 9 (7), 1247-1250
54. Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., Organocatalytic direct asymmetric aldol reactions in water. J. Am. Chem. Soc. 2006, 128 (3), 734-735
55. Luo, S.; Xu, H.; Li, J.; Zhang, L.; Cheng, J.-P., A simple primaryβtertiary diamine βBrønsted acid catalyst for asymmetric direct aldol reactions of linear aliphatic ketones. J. Am. Chem. Soc. 2007, 129 (11), 3074-3075.
56. Chen, J.-R.; Li, X.-Y.; Xing, X.-N.; Xiao, W.-J., Sterically and electronically tunable and bifunctional organocatalysts: Design and application in asymmetric aldol reaction of cyclic ketones with aldehydes. J. Org. Chem. 2006, 71 (21), 8198-8202
57. Huang, W.-P.; Chen, J.-R.; Li, X.-Y.; Cao, Y.-J.; Xiao, W.-J., Asymmetric organocatalytic direct aldol reactions of cyclohexanone with aldehydes in brine. Can. J. Chem. 2007, 85 (3), 208-213
58. Li, C.-F.; Liu, H.; Liao, J.; Cao, Y.-J.; Liu, X.-P.; Xiao, W.-J., Enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indoles. Org. Lett. 2007, 9 (10), 1847-1850
59. Li, D. P.; Guo, Y. C.; Ding, Y.; Xiao, W. J., Organocatalytic C3-selective Friedel-Crafts alkylations of indoles with ttttt-unsaturated ketones. Chem. Commun. 2006, (7), 799-801
60. Cao, Y.-J.; Lai, Y.-Y.; Wang, X.; Li, Y.-H.; Xiao, W.-J., Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts. Tetrahedron Lett. 2007, 48 (1), 21-24.
61. Ma, J. A.; Cahard, D., Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions. Chem. Rev. 2004, 104 (12), 6119-6146.
62. Kamano, Y.; Zhang, H. P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R., Convolutamydine-a, a novel bioactive hydroxyoxindole alkaloid from marine bryozoan amathia-convoluta. Tetrahedron Lett. 1995, 36 (16), 2783-2784.
63. Rodriguez, B.; Bruckmann, A.; Bolm, C., A highly efficient asymmetric organocatalytic aldol reaction in a ball mill. Chem. Eur. J. 2007, 13 (17), 4710-4722.
64. Hernandez, J. G.; Juaristi, E., Efficient ball-mill procedure in the 'green' asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides in the presence of water. Tetrahedron 2011, 67 (36), 6953-6959.
65. Huang, X.-Y.; Wang, H.-J.; Shi, J., Theoretical study on acidities of (s)-proline amide derivatives in dmso and its implications for organocatalysis. J. Phys. Chem. A 2010, 114 (2), 1068-1081.
66. Luppi, G.; Cozzi, P. G.; Monari, M.; Kaptein, B.; Broxterman, Q. B.; Tomasini, C., Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins. J. Org. Chem. 2005, 70 (18), 7418-7421.
67. Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M., Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. Angew. Chem. Int. Ed. 2005, 44 (27), 4212-4215
68. Hayashi, Y.; Obi, K.; Ohta, Y.; Okamura, D.; Ishikawa, H., Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic Michael reaction for the formation of fffff-disubstituted-amino acid derivatives. Chem. Asian J. 2009, 4 (2), 246-249.
69. Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jorgensen, K. A., Enantioselective organocatalyzed ooosulfenylation of aldehydes. Angew. Chem. Int. Ed. 2005, 44 (5), 794-797
70. Jiang, H.; Falcicchio, A.; Jensen, K. L.; Paixao, M. W.; Bertelsen, S.; Jorgensen, K. A., Target-directed organocatalysis: A direct asymmetric catalytic approach to chiral propargylic and allylic fluorides. J. Am. Chem. Soc. 2009, 131 (20), 7153-7157.
71. Ishikawa, H.; Suzuki, T.; Hayashi, Y., High-yielding synthesis of the antiinfluenza neuramidase inhibitor (-)-oseltamivir by three "One-pot" Operations. Angew. Chem. Int. Ed. 2009, 48 (7), 1304-1307.
72. Xue, F.; Zhang, S.; Liu, L.; Duan, W.; Wang, W., Organocatalytic enantioselective cross-aldol reactions of aldehydes with isatins: Formation of two contiguous quaternary centered 3-substituted 3-hydroxyindol-2-ones. Chem. Asian J. 2009, 4 (11), 1664-1667.
73. Li, X.; Deng, H.; Luo, S.; Cheng, J.-P., Organocatalytic three-component reactions of pyruvate, aldehyde and aniline by hydrogen-bonding catalysts. Eur. J. Org. Chem. 2008, (25), 4350-4356.
74. Li, P.; Wang, Y.; Liang, X.; Ye, J., Asymmetric multifunctional organocatalytic Michael addition of nitroalkanes to MM,-unsaturated ketones. Chem. Commun. 2008, (28), 3302-3304
75. Fuerst, D. E.; Jacobsen, E. N., Thiourea-catalyzed enantioselective cyanosilylation of ketones. J. Am. Chem. Soc. 2005, 127 (25), 8964-8965.
76. Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H., Asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst. Angew. Chem. Int. Ed. 2004, 43 (15), 1983-1986
77. Cobb, A. J. A.; Shaw, D. M.; Ley, S. V., 5-pyrrolidin-2-yltetrazole: A new, catalytic, more soluble alternative to proline in an organocatalytic asymmetric Mannich-type reaction. Synlett 2004, (3), 558-560.
78. Hara, N.; Nakamura, S.; Shibata, N.; Toru, T., First enantioselective synthesis of (R)-convolutamydine B and E with N-(heteroarenesulfonyl)prolinamides. Chem. Eur. J. 2009, 15 (28), 6790-6793.
79. Raj, M.; Veerasamy, N.; Singh, V. K., Highly enantioselective synthesis of 3-cycloalkanone-3-hydroxy-2-oxindoles, potential anticonvulsants. Tetrahedron Lett. 2010, 51 (16), 2157-2159.
80. Liu, Y.; Gao, P.; Wang, J.; Sun, Q.; Ge, Z.; Li, R., Primary 1,2-diamine catalysis (v): Efficient asymmetric aldol reactions of isatins with cyclohexanone. Synlett 2012, 23 (07), 1031-1034.
81. Wang, J.; Qi, C.; Ge, Z.; Cheng, T.; Li, R., Efficient direct asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones catalyzed by vicinal primary-diamine salts. Chem. Commun. 2010, 46 (12), 2124-2126.
82. Wang, J.; Wang, X.; Ge, Z.; Cheng, T.; Li, R., Highly enantioselective Michael addition of cyclopentanone with chalcones via novel di-iminium mechanism. Chem. Commun. 2010, 46 (10), 1751-1753.
83. Liu, Y.; Wang, J.; Sun, Q.; Li, R., Chiral 1,2-diaminocyclohexane as organocatalyst for enantioselective aldol reaction. Tetrahedron Lett. 2011, 52 (28), 3584-3587.
84. Malkov, A. V.; Kabeshov, M. A.; Bella, M.; Kysilka, O.; Malyshev, D. A.; Pluháčková, K.; Kočovsk, P. P., Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: Application in the synthesis of convolutamydine A. Org. Lett. 2007, 9 (26), 5473-5476.
85. Ricci, A.; Bernardi, L.; Gioia, C.; Vierucci, S.; Robitzer, M.; Quignard, F., Chitosan aerogel: A recyclable, heterogeneous organocatalyst for the asymmetric direct aldol reaction in water. Chem. Commun. 2010, 46 (34), 6288-6290.
86. Shen, C.; Shen, F.; Xia, H.; Zhang, P.; Chen, X., Carbohydrate-derived alcohols as organocatalysts in enantioselective aldol reactions of isatins with ketones. Tetrahedron: Asymm. 2011, 22 (6), 708-712.
87. Schreiner, P. R., Metal-free organocatalysis through explicit hydrogen bonding interactions. Chem. Soc. Rev. 2003, 32 (5), 289-296
88. France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T., Nucleophilic chiral amines as catalysts in asymmetric synthesis. Chem. Rev. 2003, 103 (8), 2985-3012
89. Doyle, A. G.; Jacobsen, E. N., Small-molecule H-bond donors in asymmetric catalysis. Chem. Rev. 2007, 107 (12), 5713-5743.
90. McCooey, S. H.; Connon, S. J., Urea-and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance. Angew. Chem. Int. Ed. 2005, 44 (39), 6367-6370
91. Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L., Asymmetric Friedel-Crafts reaction of indoles with imines by an organic catalyst. J. Am. Chem. Soc. 2006, 128 (25), 8156-8157
92. Wang, J.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Duan, W.; Wang, W., Organocatalytic enantioselective conjugate additions to enones. J. Am. Chem. Soc. 2006, 128 (39), 12652-12653
93. Vakulya, B.; Varga, S.; Csampai, A.; Soos, T., Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Org. Lett. 2005, 7 (10), 1967-1969
94. Liu, T.-Y.; Cui, H.-L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z.-Q.; Chen, Y.-C., Organocatalytic and highly enantioselective direct-amination of aromatic ketones. Org. Lett. 2007, 9 (18), 3671-3674
95. Zhou, J.; Wakchaure, V.; Kraft, P.; List, B., Primary-amine-catalyzed enantioselective intramolecular aldolizations. Angew. Chem. Int. Ed. 2008, 47 (40), 7656-7658.
96. Tian, S. K.; Chen, Y. G.; Hang, J. F.; Tang, L.; McDaid, P.; Deng, L., Asymmetric organic catalysis with modified cinchona alkaloids. Acc. Chem. Res. 2004, 37 (8), 621-631.
97. Samanta, S.; Zhao, C.-G., Organocatalytic enantioselective synthesis of)-hydroxy phosphonates. J. Am. Chem. Soc. 2006, 128 (23), 7442-7443
98. Dodda, R.; Zhao, C.-G., Organocatalytic highly enantioselective synthesis of secondary ss-hydroxyphosphonates. Org. Lett. 2006, 8 (21), 4911-4914
99. Samanta, S.; Perera, S.; Zhao, C.-G., Organocatalytic enantioselective synthesis of both diastereomers of oo-hydroxyphosphinates. J. Org. Chem. 2010, 75 (4), 1101-1106
100. Dodda, R.; Zhao, C.-G., Organocatalytic enantioselective synthesis of secondary α-hydroxycarboxylates. Synlett 2007, 2007 (10), 1605-1609.
101. Guo, Q.; Bhanushali, M.; Zhao, C.-G., Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: Highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones. Angew. Chem. Int. Ed. 2010, 49 (49), 9460-9464.
102. Garden, S. J.; da Silva, R. B.; Pinto, A. C., A versatile synthetic methodology for the synthesis of tryptophols. Tetrahedron 2002, 58 (42), 8399-8412
103. Garden, S. J.; Torres, J. C.; Ferreira, A. A.; Silva, R. B.; Pinto, A. C., A modified sandmeyer methodology and the synthesis of (+/-)-convolutamydine a. Tetrahedron Lett. 1997, 38 (9), 1501-1504
104. Braude, F.; Lindwall, H. G., Condensations of isatin with acetone by the Knoevenagel method. J. Am. Chem. Soc. 1933, 55, 325-327.
105. Goehring, R. R.; Sachdeva, Y. P.; Pisipati, J. S.; Sleevi, M. C.; Wolfe, J. F., Photoinduced cyclizations of monoanions and dianions of N-acyl-orthochloranilines and N-acyl-ortho-chlorobenzylamines as general-methods for the synthesis of oxindoles and 1,4-dihydro-3(2h)-isoquinolinones. J. Am. Chem. Soc. 1985, 107 (2), 435-443
106. Rasmussen, H. B.; MacLeod, J. K., Total synthesis of donaxaridine. J. Nat. Prod. 1997, 60 (11), 1152-1154
107. Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L., Oxidized welwitindolinones from terrestrial fischerella spp. J. Nat. Prod. 1999, 62 (4), 569-572
108. Tokunaga, T.; Hume, W. E.; Nagamine, J.; Kawamura, T.; Taiji, M.; Nagata, R., Structure-activity relationships of the oxindole growth hormone secretagogues. Bioorg. Med. Chem. Lett. 2005, 15 (7), 1789-1792.
109. Mei, K.; Zhang, S.; He, S.; Li, P.; Jin, M.; Xue, F.; Luo, G.; Zhang, H.; Song, L.; Duan, W.; Wang, W., (S)-pyrrolidine sulfonamide catalyzed asymmetric direct aldol reactions of aryl methyl ketones with aryl aldehydes. Tetrahedron Lett. 2008, 49 (17), 2681-2684
110. Dodda, R.; Zhao, C.-G., Lproline-catalyzed one-pot three-component reaction for the synthesis of cc-alkoxy ketones. Synthesis 2006, (19), 3238-3242.
111. Erkizan, H. V.; Kong, Y.; Merchant, M.; Schlottmann, S.; Barber-Rotenberg, J. S.; Yuan, L.; Abaan, O. D.; Chou, T.-H.; Dakshanamurthy, S.; Brown, M. L.; Uren, A.; Toretsky, J. A., A small molecule blocking oncogenic protein EWS-FLI1 interaction with RNA helicase a inhibits growth of Ewing's sarcoma. Nat. Med. 2009, 15 (7), 750-U8.
112. Allu, S.; Molleti, N.; Panem, R.; Singh, V. K., Enantioselective organocatalytic aldol reaction of unactivated ketones with isatins. Tetrahedron Lett. 2011, 52 (32), 4080-4083.
113. Kohler, M. C.; Yost, J. M.; Garnsey, M. R.; Coltart, D. M., Direct carboncarbon bond formation via soft enolization: A biomimetic asymmetric mannich reaction of phenylacetate thioesters. Org. Lett. 2010, 12 (15), 3376-3379
114. Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R., A unique approach to the concise synthesis of highly optically active spirooxazolines and the discovery of a more potent oxindole-type phytoalexin analogue. J. Am. Chem. Soc. 2010, 132 (43), 15328-15333.
115. Kang, G.; Jiang, J.; Liu, H.; Wu, H., Asymmetric organocatalytic synthesis of beta-hydroxyynones with a quaternary carbon center under aqueous conditions. J. Brazil. Chem. Soc. 2012, 23 (1), 5-10.
116. Hu, S. K.; Neckers, D. C., Photochemical reactions of alkyl phenylglyoxylates. J. Org. Chem. 1996, 61 (18), 6407-6415
117. DiMauro, E. F.; Kozlowski, M. C., Development of bifunctional salen catalysts: Rapid, chemoselective alkylations of α-ketoesters. J. Am. Chem. Soc. 2002, 124 (43), 12668-12669.
118. Paradowska, J.; Stodulski, M.; Mlynarski, J., Catalysts based on amino acids for asymmetric reactions in water. Angew. Chem. Int. Ed. 2009, 48 (24), 4288-4297.
119. Liu, G.-G.; Zhao, H.; Lan, Y.-B.; Wu, B.; Huang, X.-F.; Chen, J.; Tao, J.-C.; Wang, X.-W., Asymmetric cross aldol addition of isatins with α, β-unsaturated ketones catalyzed by a bifunctional Brønsted acid-Brønsted base organocatalyst. Tetrahedron 2012, 68 (20), 3843-3850.
120. 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
121. 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 (46), 8748-8758
122. 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, (12), 2209-2219
123. Lin, H.; Danishefsky, S. J., Gelsemine: A thought-provoking target for total synthesis. Angew. Chem. Int. Ed. 2003, 42 (1), 36-51
124. Trost, B. M.; Brennan, M. K., Asymmetric syntheses of oxindole and indole spirocyclic alkaloid natural products. Synthesis 2009, (18), 3003-3025
125. 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 (9), 1381-1407.
126. Guang, J.; Guo, Q.; Zhao, J. C.-G., Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions. Org. Lett. 2012, 14 (12), 3174-3177.
127. Zhong, F.; Yao, W.; Dou, X.; Lu, Y., Enantioselective construction of 3-hydroxy oxindoles via decarboxylative addition of hh-ketoacids to isatins. Org. Lett. 2012, 14 (15), 4018-4021.
128. Popp, F. D., Potential anticonvulsants.5. The condensation of isatins with C-acetyl heterocyclic-compounds. J. Heterocyclic Chem. 1982, 19 (3), 589-592
129. Beeson, C. C.; Rohrer, B.; Perron, N. R. Compositions and methods for the treatment of degenerative diseases. WO2011119869A1, 2011.
130. Liu, H.; Wu, H.; Luo, Z.; Shen, J.; Kang, G.; Liu, B.; Wan, Z.; Jiang, J., Regioselectivity-reversed asymmetric aldol reaction of 1,3-dicarbonyl compounds. Chem. Eur. J. 2012, 18 (38), 11899-903.
131. Knoevenagel, E., Preparation of ethylic benzylideneacetoacetate. Ber. 1896, 29, 172-174.
132. Bode, S. E.; Drochner, D.; Mueller, M., Synthesis, biosynthesis and absolute configuration of Vioxanthin. Angew. Chem. Int. Ed. 2007, 46 (31), 5916-5920.
133. Snider, B. B.; Song, F. B., Total synthesis of (-)-salicylihalamide A. Org. Lett. 2001, 3 (12), 1817-1820.
134. Hara, N.; Nakamura, S.; Funahashi, Y.; Shibata, N., Organocatalytic enantioselective decarboxylative addition of malonic acids half thioesters to isatins. Adv. Synth. Catal. 2011, 353 (16), 2976-2980.
135. Hibino, S.; Choshi, T., Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat. Prod. Rep. 2001, 18 (1), 66-87
136. Jensen, B. S., Bms-204352: A potassium channel opener developed for the treatment of stroke. CNS Drug. Rev. 2002, 8 (4), 353-360
137. Sundberg, R. J., The chemistry of indoles (Organic Chemistry; a series of monographs, vol. 18). Academic: 1970; p 489 pp
138. Sundberg, R. J.; Editor, Indoles. Academic: 1996; p 190 pp
139. Popp, F. D.; Parson, R.; Donigan, B. E., Potential anticonvulsants. Iii. The condensation of isatin with cyclic ketones. J. Heterocyclic Chem. 1980, 17, 1329-30
140. Bhattacharya, S. K.; Chakrabarti, A., Doserelated proconvulsant and anticonvulsant activity of isatin, a putative biological factor, in rats. Indian J. Exp. Biol. 1998, 36 (1), 118-21
141. Bekircan, O.; Kahveci, B.; Kucuk, M., Synthesis and anticancer evaluation of some new unsymmetrical 3,5-diaryl-4h-1,2,4-triazole derivatives. Turk. J. Chem. 2006, 30, 29-40.
142. Avendaño, C.; Menéndez, J. C., Synthetic studies on Nmethylwelwitindolinone C isothiocyanate (welwistatin) and related substructures. Curr. Org. Synth. 2004, 1 (1), 65-82
143. Menéndez, J. C., Chemistry of the welwitindolinones. Top. Heterocycl. Chem. 2007, 11, 63-101
144. Ruiz, M.; López-Alvarado, P.; Menéndez, J. C., Concise and very efficient synthesis of the N-Methylwelwistatin tetracyclic core based on an anionic domino process. Org. Biomol. Chem. 2010, 8 (20), 4521-4523.
145. Bhat, V.; Allan, K. M.; Rawal, V. H., Total synthesis of N-methylwelwitindolinone D isonitrile. J. Am. Chem. Soc. 2011, 133 (15), 5798-5801.
146. Monde, K.; Sasaki, K.; Shirata, A.; Takasugi, M., Brassicanal C and 2-dioxindoles from cabbage. Phytochemistry 1991, 30 (9), 2915-2917
147. Suchy, M.; Kutschy, P.; Monde, K.; Goto, H.; Harada, N.; Takasugi, M.; Dzurilla, M.; Balentova, E., Synthesis, absolute configuration, and enantiomeric enrichment of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin, and its oxazoline analog. J. Org. Chem. 2001, 66 (11), 3940-3947
148. Bui, T.; Syed, S.; Barbas, C. F., III, Thiourea-catalyzed highly enantio-and diastereoselective additions of oxindoles to nitroolefins: Application to the formal synthesis of (+)-physostigmine. J. Am. Chem. Soc. 2009, 131 (25), 8758-8759.
149. Corey, E. J.; Guzmán-Pérez, A., The catalytic enantioselective construction of molecules with quaternary carbon stereocenters. Angew. Chem. Int. Ed. 1998, 37 (4), 388-401
150. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N., Enantioselective catalytic formation of quaternary stereogenic centers. Eur. J. Org. Chem. 2007, (36), 5969-5994
151. Liu, Y.-L.; Wang, B.-L.; Cao, J.-J.; Chen, L.; Zhang, Y.-X.; Wang, C.; Zhou, J., Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via MoritáBaylisHillman reaction. J. Am. Chem. Soc. 2010, 132 (43), 15176-15178
152. Itoh, J.; Han, S. B.; Krische, M. J., Enantioselective allylation, crotylation, and reverse prenylation of substituted isatins: Iridium-catalyzed C-C bond-forming transfer hydrogenation. Angew. Chem. Int. Ed. 2009, 48 (34), 6313-6316
153. Zhu, Q.; Lu, Y., Stereocontrolled creation of all-carbon quaternary stereocenters by organocatalytic conjugate addition of oxindoles to vinyl sulfone. Angew. Chem. Int. Ed. 2010, 49 (42), 7753-7756
154. Mohr, J. T.; Krout, M. R.; Stoltz, B. M., Natural products as inspiration for the development of asymmetric catalysis. Nature 2008, 455 (7211), 323-332
155. Riant, O.; Hannedouche, J., Asymmetric catalysis for the construction of quaternary carbon centres: Nucleophilic addition on ketones and ketimines. Org. Biomol. Chem. 2007, 5 (6), 873-888.
156. Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M., Enantioselective synthesis of SM-130686 based on the development of asymmetric Cu(I)F catalysis to access 2-oxindoles containing a tetrasubstituted carbon. J. Am. Chem. Soc. 2009, 131 (20), 6946-6948
157. Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K., Catalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles. Angew. Chem. Int. Ed. 2010, 49 (4), 744-747
158. 2+ Diaqua complexes as catalysts. Org. Lett. 2011, 13 (9), 2314-2317
159. Zhong, F.; Chen, G.-Y.; Lu, Y., Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: Facile creation of 3-hydroxy-2-oxindoles. Org. Lett. 2011, 13 (1), 82-85
160. Grant, C. D.; Krische, M. J., Protecting-group-free synthesis of 3-tert-prenylated oxindoles: Contiguous all-carbon quaternary centers via tertiary neopentyl substitution. Org. Lett. 2009, 11 (20), 4485-4487
161. Guo, X.; Huang, H.; Yang, L.; Hu, W., Trapping of oxonium ylide with isatins: Efficient and stereoselective construction of adjacent quaternary carbon centers. Org. Lett. 2007, 9 (23), 4721-4723.
162. Palomo, C.; Oiarbide, M.; Laso, A., Recent advances in the catalytic asymmetric nitroaldol (henry) reaction. Eur. J. Org. Chem. 2007, (16), 2561-2574
163. Palomo, C.; Oiarbide, M.; Mielgo, A., Unveiling reliable catalysts for the asymmetric nitroaldol (Henry) reaction. Angew. Chem. Int. Ed. 2004, 43 (41), 5442-5444
164. Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C., Catalytic asymmetric Henry reaction. Tetrahedron: Asymm. 2006, 17 (24), 3315-3326.
165. Ono, N.; Editor, The nitro group in organic synthesis. John Wiley & Sons, Inc.: 2001; p 392 pp
166. Luzzio, F. A., The Henry reaction: Recent examples. Tetrahedron 2001, 57 (6), 915-945
167. Seebach, D.; Lehr, F., 66,-doubly deprotonated nitroalkanes-enhancement of C-nucleophilicity of ni tronates. Angew. Chem. Int. Ed. 1976, 15 (8), 505-506
168. Eyer, M.; Seebach, D., L-2-nitro-1,3-alkanediols by stereoselective addition of nitroethanol to aldehydes-on the asymmetric electrophilic addition to double-bonds. J. Am. Chem. Soc. 1985, 107 (12), 3601-3606
169. 3N: An efficient promoter for the nitroaldol (Henry) reaction. J. Org. Chem. 1999, 64 (12), 4298-4303
170. Bandini, M.; Sinisi, R.; Umani-Ronchi, A., Enantioselective organocatalyzed Henry reaction with fluoromethyl ketones. Chem. Commun. 2008, (36), 4360-4362
171. Saa, J. M.; Tur, F.; Gonzalez, J., Lanthanide (iii) salt complexes: Arrayed acid-base networks for enantioselective catalysis. The nitroaldol reaction upon aldehydes and trifluoromethylketones. Chirality 2009, 21 (9), 836-842
172. Tur, F.; Saa, J. M., Direct, catalytic enantioselective nitroaldol (Henry) reaction of trifluoromethyl ketones: An asymmetric entry to tt-trifluoromethylsubstituted quaternary carbons. Org. Lett. 2007, 9 (24), 5079-5082.
173. Liu, L.; Zhang, S.; Xue, F.; Lou, G.; Zhang, H.; Ma, S.; Duan, W.; Wang, W., Catalytic enantioselective Henry reactions of isatins: Application in the concise synthesis of (S)-()-spirobrassinin. Chem. Eur. J. 2011, 17 (28), 7791-7795.
174. Pedras, M. S. C.; Okanga, F. I.; Zaharia, I. L.; Khan, A. Q., Phytoalexins from crucifers: Synthesis, biosynthesis, and biotransformation. Phytochemistry 2000, 53 (2), 161-176.
175. Pedras, M. S. C.; Hossain, M., Metabolism of crucifer phytoalexins in sclerotinia sclerotiorum: Detoxification of strongly antifungal compounds involves glucosylation. Org. Biomol. Chem. 2006, 4 (13), 2581-2590.
176. Mehta, R. G.; Liu, J. F.; Constantinou, A.; Hawthorne, M.; Pezzuto, J. M.; Moon, R. C.; Moriarty, R. M., Structure-activity-relationships of brassinin in preventing the development of carcinogen-induced mammary lesions in organ-culture. Anticancer Res. 1994, 14 (3A), 1209-1213.
177. Baur, R.; Staedler, E.; Monde, K.; Takasugi, M., Phytoalexins from Brassica (Cruciferae) as oviposition stimulants for the cabbage root fly, delia radicum. Chemoecology 1998, 8 (4), 163-168.
178. Zhang, Y.; Jun Li, Z.; Sen Xu, H.; Zhang, Y.; Wang, W., Organocatalytic asymmetric Henry reaction of isatins: Highly enantioselective synthesis of 3-hydroxy-2-oxindoles. RSC Adv. 2011, 1 (3), 389-392.
179. Takasugi, M.; Monde, K.; Katsui, N.; Shirata, A., Studies on stress metabolites.6. Spirobrassinin, a novel sulfur-containing phytoalexin from the daikon rhaphanus-sativus l var hortensis (cruciferae). Chem. Lett 1987, (8), 1631-1632
180. Monde, K.; Osawa, S.; Harada, N.; Takasugi, M.; Suchy, M.; Kutschy, P.; Dzurilla, M.; Balentova, E., Synthesis and absolute stereochemistry of a cruciferous phytoalexin, (-)-spirobrassinin. Chem. Lett 2000, (8), 886-887
181. Kutschy, P.; Suchy, M.; Monde, K.; Harada, N.; Maruskova, R.; Curillova, Z.; Dzurilla, M.; Miklosova, M.; Mezencev, R.; Mojzis, J., Spirocyclization strategy toward indole phytoalexins. The first synthesis of (+/-)-1-methoxyspirobrassinin, (+/-)-1-methoxyspirobrassinol, and (+/-)-1-methoxyspirobrassinol methyl ether. Tetrahedron Lett. 2002, 43 (52), 9489-9492.
182. Li, M.-Q.; Zhang, J.-X.; Huang, X.-F.; Wu, B.; Liu, Z.-M.; Chen, J.; Li, X.-D.; Wang, X.-W., Asymmetric nitroaldol reactions of nitroalkanes with isatins catalyzed by bifunctional cinchona alkaloid derivatives. Eur. J. Org. Chem. 2011, 2011 (27), 5237-5241.
183. Prathima, P. S.; Srinivas, K.; Balaswamy, K.; Arundhathi, R.; Reddy, G. N.; Sridhar, B.; Rao, M. M.; Likhar, P. R., Biscinchona alkaloid catalyzed Henry reaction of isatins: Enantioselective synthesis of 3-hydroxy-3-(nitromethyl)indolin-2-ones. Tetrahedron: Asymm. 2011, 22 (24), 2099-2103.
184. Masson, G.; Housseman, C.; Zhu, J., The enantioselective Morita-Baylis-Hillman reaction and its aza counterpart. Angew. Chem. Int. Ed. 2007, 46 (25), 4614-4628
185. Basavaiah, D.; Rao, K. V.; Reddy, R. J., The Baylis-Hillman reaction: A novel source of attraction, opportunities, and challenges in synthetic chemistry. Chem. Soc. Rev. 2007, 36 (10), 1581-1588
186. Krishna, P. R.; Sachwani, R.; Reddy, P. S., Asymmetric Baylis-Hillman reaction: An enchanting expedition. Synlett 2008, (19), 2897-2912
187. Carrasco-Sánchez, V.; Simirgiotis, M. J.; Santos, L. S., The Morita-Baylis-Hillman reaction: Insights into asymmetry and reaction mechanisms by electrospray ionization mass spectrometry. Molecules 2009, 14 (10), 3989-4021
188. Wei, Y.; Shi, M., Multifunctional chiral phosphine organocatalysts in catalytic asymmetric Morita-Baylis-Hillman and related reactions. Acc. Chem. Res. 2010, 43 (7), 1005-1018.
189. Shintani, R.; Hayashi, S.-Y.; Murakami, M.; Takeda, M.; Hayashi, T., Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of cc-methylidene-valerolactones with isatins. Org. Lett. 2009, 11 (16), 3754-3756
190. Nakamura, S.; Hara, N.; Nakashima, H.; Kubo, K.; Shibata, N.; Toru, T., Enantioselective synthesis of (R)-convolutamydinéa with new N-heteroarylsulfonylprolinamides. Chem. Eur. J. 2008, 14 (27), 8079-8081
191. Itoh, T.; Ishikawa, H.; Hayashi, Y., Asymmetric aldol reaction of acetaldehyde and isatin derivatives for the total syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B. Org. Lett. 2009, 11 (17), 3854-3857
192. 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 (5), 833-838
193. Chauhan, P.; Chimni, S. S., Asymmetric addition of indoles to isatins catalyzed by bifunctional modified cinchona alkaloid catalysts. Chem. Eur. J. 2010, 16 (26), 7709-7713.
194. Sano, D.; Nagata, K.; Itoh, T., Catalytic asymmetric hydroxylation of oxindoles by molecular oxygen using a phase-transfer catalyst. Org. Lett. 2008, 10 (8), 1593-1595
195. Bui, T.; Candeias, N. R.; Barbas, C. F., III, Dimeric quinidine-catalyzed enantioselective aminooxygenation of oxindoles: An organocatalytic approach to 3-hydroxyoxindole derivatives. J. Am. Chem. Soc. 2010, 132 (16), 5574-5575.
196. Jia, Y.-X.; Hillgren, J. M.; Watson, E. L.; Marsden, S. P.; Kuendig, E. P., Chiral N-heterocyclic carbene ligands for asymmetric catalytic oxindole synthesis. Chem. Commun. 2008, (34), 4040-4042.
197. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S., Chiral amine-catalyzed asymmetric Baylis-Hillman reaction: A reliable route to highly enantiomerically enriched (hh-methylene----hydroxy)esters. J. Am. Chem. Soc. 1999, 121 (43), 10219-10220
198. Nakano, A.; Takahashi, K.; Ishihara, J.; Hatakeyama, S., II-isocupreidine-catalyzed Baylis-Hillman reaction of chiral N-Boc----amino aldehydes. Org. Lett. 2006, 8 (23), 5357-5360.
199. Wang, C.-C.; Wu, X.-Y., Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita-Baylis-Hillman reaction of isatins. Tetrahedron 2011, 67 (16), 2974-2978.
200. Feng, J.; Yan, W.; Wang, D.; Li, P.; Sun, Q.; Wang, R., The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids. Chem. Commun. 2012, 48 (64), 8003-8005.