Binaphthyl-derived mono-, Bi- and multi-functional lewis and brønsted base organocatalysts: A new vista for asymmetric synthesis

Current Organic Chemistry

Volumn 15, Issue 13, 2011, Pages 2282-2310

  Freund, Matthias ^a   Schenker, Sebastian ^a   Zamfir, Alexandru ^a   Tsogoeva, Svetlana B ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Asymmetric organocatalysis; Bi multi functional catalysis; Binaphthyl derived organocatalysts; Br nsted bases; Lewis bases; Urea thioureas

Indexed keywords

CATALYSTS; HYDROGEN BONDS; METABOLISM; PHOSPHORUS COMPOUNDS; RATE CONSTANTS; UREA;

ASYMMETRIC ORGANOCATALYSIS; BASE CATALYSIS; BI-/MULTI-FUNCTIONAL CATALYSE; BINAPHTHYL; BINAPHTHYL-DERIVED ORGANOCATALYST; BRØNSTED BASE; LEWIS BASE; MULTI-FUNCTIONAL; ORGANOCATALYSTS; UREA/THIOUREA;

CATALYSIS;

EID: 79959286465     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211796150750     Document Type: Review

References (136)

1. For general reviews on asymmetric organocatalyis, see: 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. Special Issue on Asymmetric Organocatalysis (Ed. Houk, K.N.; List, B.): Acc. Chem. Res., 2004, 37, Issue 8, 487-631.
4. Berkessel, A.; Gröger, H. in Asymmetric Organocatalysis, Wiley-VCH: Weinheim, 2005.
5. List, B.; Yang, J.W. The organic approach to asymmetric catalysis. Science, 2006, 313, 1584-1586.
6. Enantioselective Organocatalysis (Ed. Dalko, P. I.), Wiley-VCH: Weinheim, 2007.
7. Pellissier, Asymmetric organocatalysis. H. Tetrahedron, 2007, 63, 9267-9331.
8. Dondoni, A.; Massi, A. Angew. Chem. Int. Ed., 2008, 47, 4638-4660.
9. Seayad, J.; List, B. Asymmetric organocatalysis. Org. Biomol. Chem., 2005, 3, 719-724.
10. For reviews, see: Schreiner, P. R. Metal-Free organocatalysis through explicit hydrogen bonding interactions. Chem. Soc. Rev., 2003, 32, 289-296.
11. Takemoto, Y. Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors. Org. Biomol. Chem., 2005, 3, 4299-4306.
12. Taylor, M. S.; Jacobsen, E. N. Asymmetric catalysis by chiral hydrogen-bond donors. Angew. Chem. Int. Ed., 2006, 45, 1520-1543.
13. Connon, S. J. Organocatalysis mediated by (thio) urea derivatives Chem. Eur. J., 2006, 12, 5418-5427.
14. Doyle, A. G.; Jacobsen, E. N. Small-molecule H-bond donors in asymmetric catalysis. Chem. Rev., 2007, 107, 5713-5743.
15. For reviews, see: List, B. The ying and yang of asymmetric aminocatalysis. Chem. Commun., 2006, 8, 819-824.
16. Mukherjee, S.; Yang, J.W.; Hoffmann, S.; List, B. Asymmetric enamine catalysis. Chem. Rev., 2007, 107, 5471-5569.
17. For reviews, see: Akiyama, T.; Itoh, J.; Fuchibe, K., Recent progress in chiral brønsted acid catalysis. Adv. Synth. Catal., 2006, 348, 999-1010.
18. Akiyama, T. Stronger brønsted acids. Chem. Rev., 2007, 107, 5744-5758.
19. Connon, S. Asymmetric organocatalytic reductions mediated by dihydropyridines. Org. Biomol. Chem., 2007, 5, 3407-3417.
20. Kano, T.; Maruoka, K. Design of chiral bifunctional secondary amine catalysts for asymmetric enamine catalysis. Chem. Commun., 2008, 5465-5473.
21. Terada, M. Binaphthol-Derived phosphoric acid as a versatile catalyst for enantioselective carbon-carbon bond forming reactions. Chem. Commun., 2008, 4097-4112.
22. Ueda, M.; Kano, T.; Maruoka, K. Organocatalyzed direct asymmetric α-halogenation of carbonyl compounds. Org. Biomol. Chem., 2009, 7, 2005-2012.
23. Maruoka, K.; Ooi, T.; Kano, T. Design of chiral organocatalysts for practical asymmetric synthesis of amino acid derivatives. Chem. Commun., 2007, 1487-1495.
24. Ooi, T.; Maruoka, K. Angew. Chem. Int. Ed., 2007, 46, 4222-4266.
25. Hupe, D. J. Enzyme Reactions involving imine formations. In New Comprehensive Biochemistry, Vol. 6 (Ed.: Page, M. I.), Elsevier, Amsterdam, 1984, 271-301.
26. For reviews, see: Peng, F.; Shao, Z. Advances in asymmetric organocatalytic reactions catalyzed by chiral primary amines. J. Mol. Catal. A, 2008, 285, 1-13.
27. Xu, L.-W.; Luo, J.; Lu, Y. Asymmetric catalysis with chiral primary amine-based organocatalysts. Chem. Commun., 2009, 1807-1821.
28. For examples of asymmetric organocatalysis based on the primary amine functionality, developed in our group, see: Tsogoeva, S. B.; Jagtap, S. B. Dual Catalyst Control in the Chiral Diamine-Dipeptide-Catalyzed Ssymmetric Michael Addition. Synlett, 2004, 2624-2626.
29. Tsogoeva, S. B.; Jagtap, S. B.; Ardemasova, Z. A.; Kalikhevich, V. N. Trends in asymmetric Michael reactions catalysed by tripeptides in combination with an achiral additive in different solvents. Eur. J. Org. Chem., 2004, 4014-4019.
30. Tsogoeva, S. B.; Wei, S. (S)-Histidine-Based dipeptides as organic catalysts for direct asymmetric aldol reactions. Tetrahedron: Asymmetry, 2005, 16, 1947-1951.
31. Tsogoeva, S. B.; Wei, S. Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts. Chem. Commun., 2006, 1451-1453.
32. Yalalov, D. A.; Tsogoeva S. B.; Schmatz S. Chiral thiourea-based bifunctional organocatalysts in the asymmetric nitro-michael addition: a joint experimental-theoretical study. Adv. Synth. Catal., 2006, 348, 826-832.
33. Wei, S.; Yalalov, D. A.; Tsogoeva S. B.; Schmatz S. New highly enantioselective thiourea-based bifunctional organocatalysts for nitro-michael addition reactions. Catal. Today, 2007, 121, 151-157.
34. Yalalov, D. A.; Tsogoeva, S. B.; Shubina, T. E.; Martynova, I. M.; Clark, T. Evidence for an enol mechanism in a highly enantioselective mannich-type reaction catalyzed by primary amine-thiourea. Angew. Chem., Int. Ed., 2008, 47, 6624-6628.
35. For reviews of enantioselective Diels-Alder reactions, see: Kagan, H. B.; Riant O. Catalytic asymmetric diels alder reactions. Chem. Rev., 1992, 92, 1007-1019.
36. Evans, D. A.; Johnson, J. S. in comprehensive asymmetric catalysis (Ed.: Jacobsen, E. N., Pfaltz, A. and Yamamoto, H.), Springer, New York, 1999, Vol. 3.
37. Corey, E. J. Catalytic Enantioselective Diels-Alder Reactions: Methods, Mechanistic Fundamentals, Pathways, and Applications Angew. Chem. Int. Ed., 2002, 41, 1650-1667.
38. Shen, J.; Tan, C.-H. Brønsted-Acid and brønsted-base catalyzed diels-alder reactions. Org. Biomol. Chem., 2008, 6, 3229-3236.
39. Merino, P; Marqués-López, B; Tejeroa, T; Herrera, R. P. Enantioselective organocatalytic diels-alder reactions. Synthesis, 2010, 1, 1-26.
40. Sakakura, A.; Suzuki, K.; Ishihara, K. Enantioselective diels-alder reaction of α-acyloxyacroleins catalyzed by chiral 1, 1'-Binaphthyl-2, 2'-diammonium salts. Adv. Synth. Catal., 2006, 348, 2457-2465.
41. Sakakura, A.; Suzuki, K.; Ishihara, K. Chiral 1, 1-Binaphthyl-2, 2-diammonium salt catalysts for the enantioselective diels- alder reaction with α-acyloxyacroleins. Org. Lett., 2006, 8, 2229-2232.
42. Miyano, S.; Nawa, M.; Hashimoto, H. Asymmetric hydrogenation of α-Acylaminoacrylic acids and esters with axially dissymmetric bisaminophosphine-rhodium complexes. Chem. Lett., 1980, 6, 729-30.
43. Kondo, K.; Kurosaki, T.; Murakami, Y. Enantioselective N-Acetylation of racemic secondary alkyl amines with chiral 2-Acetylamino-2'-diacetylamino-1,1'-binaphthyl. Synlett, 1998, 725-726.
44. Kano, T.; Tanaka, Y; Osawa, K.; Yurino, T.; Maruoka, K. Catalytic enantioselective construction of all-carbon quaternary stereocenters by an organocatalytic diels-alder reaction of α-substituted α,β-unsaturated aldehydes. Chem. Commun., 2009, 15, 1956-1958.
45. Kitamura, M., PCT Int. Appl. 2007, 33 pp. CODEN: PIXXD2 WO 2007129664 A1 20071115.
46. Kano, T.; Tanaka, Y.; Maruoka, K. Exo-selective asymmetric diels- alder reaction catalyzed by diamine salts as organocatalysts. Org. Lett., 2006, 8, 2687-2689.
47. Kano, T.; Tanaka, Y.; Maruoka, K. exo-Selective asymmetric diels-alder reaction catalyzed by diamine salts as organocatalysts. Chem. Asian J., 2007, 2, 1161-1165.
48. Comprehensive review, Covering achiral and chiral guanidines as organocatalysts: Ishikawa, T.; Kumamoto, T. Guanidines in Organic Synthesis. Synthesis, 2006, 5, 737-752.
49. Terada, M.; Ube, H.; Yaguchi, Y. Axially chiral guanidine as enantioselective base catalyst for 1, 4-Addition reaction of 1, 3-Dicarbonyl compounds with conjugated nitroalkenes. J. Am. Chem. Soc., 2006, 128, 1454-1455.
50. For recent reviews on 1,4-addition reactions catalyzed by organocatalysts, see: Tsogoeva, S. B. Recent advances in asymmetric organocatalytic 1,4- conjugate additions. Eur. J. Org. Chem., 2007, 1701-1716.
51. Almasi, D.; Alonso, D. A.; Nájera, C. Organocatalytic asymmetric conjugate additions. Tetrahedron: Asymmetry, 2007, 18, 299-365.
52. Sulzer-Mossé, S.; Alexakis, A. Chiral amines as organocatalysts for asymmetric conjugate addition to nitroolefins and vinyl sulfones via enamine activation. Chem. Commun., 2007, 3123-3135.
53. Vicario, J. L.; Badía, D.; Carrillo, L. Organocatalytic enantioselective michael and hetero-michael reactions. Synthesis, 2007, 2065-2092.
54. Terada, M.; Ikehara, T.; Ube, H. Enantioselective 1, 4-Addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine. J. Am. Chem. Soc., 2007, 129, 14112-14113.
55. Terada, M.; Nakano, M.; Ube, H. Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1, 3-dicarbonyl compounds. J. Am. Chem. Soc., 2006, 128, 16044-16045.
56. Terada, M.; Tsushima, D.; Nakano, M. Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base. Adv. Synth. Catal., 2009, 351, 2817-2821.
57. Nakano, M.; Terada, M. Acid-Base dual-functional catalysis by axially chiral guanidine in enantioselective [3+2] cycloaddition of maleate to schiff bases as a precursor of azomethine elides. Synlett, 2009, 1670-1674.
58. Ube, H.; Terada, M. Enantioselective henry (Nitroaldol) reaction catalyzed by axially chiral guanidines. Bioorg. Med. Chem. Lett., 2009, 19, 3895-3898.
59. Fleury-Brégeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Screening of chiral phosphines as catalysts for the enantioselective [3+ 2] annulations of N-tosylimines with allenic esters. Tetrahedron, 2007, 63, 11920-11927.
60. Pinto, N.; Fleury-Brégeot, N.; Marinetti, A. Enantioselective Binaphthophosphepin-promoted [3+2] annulations of N-Ts and N-DPP-imines with allenoates and 2-butynoates. Eur. J. Org. Chem., 2009, 146-151.
61. Wurz, R. P.; Fu, G. C. Catalytic Asymmetric synthesis of piperidine derivatives through the [4+2] annulation of imines with allenes. J. Am. Chem. Soc., 2005, 127, 12234-12235.
62. Tokuoka, E.; Kotani, S.; Matsunaga, H.; Ishizuka, T.; Hashimoto, S.; Nakajima, M. Asymmetric ring opening of meso-Epoxides catalyzed by the chiral phosphine oxide BINAPO. Tetrahedron: Asymmetry, 2005, 16, 2391-2392.
63. Nakajima, M.; Kotani, S.; Ishizuka, T.; Hashimoto, S. Chiral phosphine oxide BINAPO as a catalyst for enantioselective allylation of aldehydes with allyltrichlorosilanes. Tetrahedron Lett., 2005, 46, 157-159.
64. Kotani, S.; Hashimoto, S.; Nakajima, M. Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by the chiral phosphine oxide BINAPO. Synlett, 2006, 1116-1118.
65. Kotani, S.; Hashimoto, S.; Nakajima, M. Chiral phosphine oxide BINAPO as a lewis base catalyst for asymmetric allylation and aldol reaction of trichlorosilyl compounds. Tetrahedron, 2007, 63, 3122-3132.
66. Kotani, S.; Shimoda, Y.; Sugiura, M.; Nakajima, M. Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst. Tetrahedron Lett., 2009, 50, 4602-4605.
67. Sugiura, M.; Kumahara, M.; Nakajima, M.; Asymmetric synthesis of 4H-1, 3-Oxazines: enantioselective reductive cyclization of N-Acylated β-Amino enones with trichlorosilane catalyzed by chiral lewis bases. Chem. Commun., 2009, 3585-3587.
68. Shimoda, Y.; Tando, T.; Kotani, S.; Sugiura, M.; Nakajima, M. Enantioselective aldol reaction of silyl ketene acetals promoted by a lewis base-activated lewis acid catalyst. Tetrahedron: Asymmetry, 2009, 20, 1369-1370.
69. Denmark, S. E.; Wynn, T. Lewis base activation of lewis acids. addition of silyl ketene acetals to aldehydes. J. Am. Chem. Soc., 2001, 123, 6199-6200.
70. Denmark, S.; Bui, T. Mechanistic insights into the chiral phosphoramidecatalyzed, enantioselective crossed-aldol reactions of aldehydes. J. Org. Chem., 2005, 70, 10393-10399.
71. Denmark, S.; Wilson, T.; Burk, M.; Heemstra, J. Enantioselective construction of quaternary stereogenic carbons by the lewis base catalyzed additions of silyl ketene imines to aldehydes. J. Am. Chem. Soc., 2007, 129, 14864-14865.
72. Denmark, S.; Heemstra, J. Lewis base activation of lewis acids. catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes. J. Org. Chem., 2007, 72, 5668-5688.
73. For selected reports on asymmetric organocatalytic reductions of imines, see: Malkov, A. V.; Stewart Liddon, A. J. P.; Ramírez-López, P.; Bendová, L.; Haigh, D.; Kočovský, P. Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines. Angew. Chem. Int. Ed., 2006, 45, 1432-1435.
74. Wang, Z.; Ye, X.; Wei, S.; Wu, P.; Zhang, A.; Sun, J. A highly enantioselective lewis basic organocatalyst for reduction of Naryl imines with unprecedented substrate spectrum. Org. Lett., 2006, 8, 999-1001.
75. Onomura, O.; Kouchi, Y.; Iwasaki, F.; Matsumura, Y. New organic activators for the enantioselective reduction of aromatic imines with trichlorosilane. Tetrahedron Lett., 2006, 47, 3751-3754.
76. Baudequin, C.; Chaturvedi, D.; Tsogoeva, S. B. Organocatalysis with chiral formamides: asymmetric allylation and reduction of imines. Eur. J. Org. Chem., 2007, 2623-2629.
77. Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Enantioselective brønsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines. Org. Lett., 2005, 7, 3781-3783.
78. Hoffmann, S.; Seayad, A. M.; List, B. A powerful brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines. Angew. Chem. Int. Ed., 2005, 44, 7424-7427.
79. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. Enantioselective organocatalytic reductive amination. J. Am. Chem. Soc., 2006, 128, 84-86.
80. Guizzetti, S.; Benaglia, M.; Celentano, G. 1,1- Binaphthyldiamine-Based lewis bases as readily available and efficient organocatalysts for the reduction of N-Aryl and N-Alkyl ketimines. Eur. J. Org. Chem., 2009, 3683-3687
81. Guizzetti, S.; Benaglia, M.; Cozzi, F.; Rossi, S.; Celentano, G. enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral lewis bases. Chirality, 2009, 21, 233-238.
82. Lin, J. H.; Che, C. M.; Lai, T. F.; Poon, C. K.; Cui, Y. X. An approach to chiral metal catalysts; the synthesis and X-ray crystal structures of a chiral tetradentate binaphthyl bis-Amide ligand and its Osmium(VI)-oxo derivative. Chem. Commun., 1991, 7, 468-470.
83. Gryko, D.; Kowalczyk, B.; Zawadzki, L. Bisprolinediamides with the binaphthyl backbone as organocatalysts for the direct asymmetric aldol reaction. Synlett, 2006, 1059-1062.
84. Xiong, Y.; Huang, X.; Gou, S.; Huang, J.; Wen, Y.; Feng, X. Enantioselective cyanosilylation of ketones catalyzed by a nitrogen-containing bifunctional catalyst. Adv. Synth. Catal., 2006, 348, 538-544.
85. Guillena, G.; del Carmen Hita, M.; Nájera, C. BINAM-Prolinamides as recoverable catalysts in the direct aldol condensation. Tetrahedron: Asymmetry, 2006, 17, 729-733.
86. Guillena, G.; del Carmen Hita, M.; Nájera, C. High acceleration of the direct aldol reaction cocatalyzed by BINAMprolinamides and benzoic acid in aqueous media. Tetrahedron: Asymmetry 2006, 17, 1493-1497.
87. Guillena, G.; del Carmen Hita, M.; Nájera, C.; Viozquez, S. Solvent-Free asymmetric direct aldol reactions organocatalysed by recoverable (Sa)-Binam-l-prolinamide. Tetrahedron: Asymmetry, 2007, 18, 2300-2304.
88. Guillena, G.; del Carmen Hita, M.; Nájera, C.; Viozquez, S. A Highly efficient solvent-free asymmetric direct aldol reaction organocatalyzed by recoverable (S)-Binam-l-Prolinamides. ESI-MS evidence of the enamine-iminium formation. J. Org. Chem., 2008, 73, 5933-5943.
89. Ma, G.-N.; Zhang, Y.-P.; Shi, M. L-Proline diamides with an axially chiral binaphthylene backbone as efficient organocatalysts for direct asymmetric aldol reactions: the effect of acetic acid. Synthesis, 2007, 2, 197-208.
90. Bradshaw, B.; Etxebarria-Jardi, G.; Bonjoch, J.; Viózquez, S.; Guillena, G.; Nájera, C. Efficient solvent-free robinson annulation protocols for the highly enantioselective synthesis of the wieland-miescher ketone and analogues. Adv. Synth. Catal., 2009, 351, 2482-2490.
91. Ma, G.-N.; Cao, S.-H.; Shi, M. Chiral Phosphine-catalyzed regio- and enantioselective allylic amination of morita-baylis-hillman acetates. Tetrahedron: Asymmetry, 2009, 20, 1086-1092.
92. Hou, Z.; Wang, J.; Liu, X.; Feng, X. Highly enantioselective strecker reaction of ketoimines catalyzed by an organocatalyst from (S)-BINOL and Lprolinamide. Chem. Eur. J., 2008, 14, 4484-4486.
93. Giuzetti, S.; Benaglia, M.; Pignataro, L.; Puglisi, A. A multifunctional proline-based organic catalyst for enantioselective aldol reactions. Tetrahedron: Asymmetry, 2006, 17, 2754-2760.
94. Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K. anti-Selective direct asymmetric mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. J. Am. Chem. Soc., 2005, 127, 16408-16409.
95. Kano, T.; Yamaguchi, Y.; Maruoka, K. A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric antiselective mannich reactions and syn-selective cross-aldol reactions. Chem. Eur. J., 2009, 15, 6678-6687.
96. Kano, T.; Yamaguchi, Y.; Maruoka, K. A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric mannich reactions of N-Boc-Protected imines. Angew. Chem. Int. Ed., 2009, 48, 1838-1840.
97. Kano, T.; Yamamoto, A.; Shirozu, F.; Maruoka, K. Enantioselectivity switch in direct asymmetric aminoxylation catalyzed by binaphthyl-based chiral secondary amines. Synthesis, 2009, 9, 1557-1563.
98. Kano, T.; Yamaguchi, Y.; Tanaka, Y.; Maruoka, K. syn-Selective and enantioselective direct cross-aldol reactions between aldehydes catalyzed by an axially chiral amino sulfonamide. Angew. Chem. Int. Ed., 2007, 46, 1738-1740.
99. Kano, T.; Yamamoto, A.; Maruoka, K. Direct asymmetric aminoxylation reaction catalyzed by a binaphthyl-based chiral amino sulfonamide with high catalytic performance. Tetrahedron Lett., 2008, 49, 5369-5371.
100. Kano, T.; Ueda, M.; Takai, J.; Maruoka, K. Direct asymmetric hydroxyamination reaction catalyzed by an axially chiral secondary amine catalyst. J. Am. Chem. Soc., 2006, 128, 6046-6047.
101. Kano, T.; Ueda, M.; Maruoka, K. Direct asymmetric iodination of aldehydes using an axially chiral bifunctional amino alcohol catalyst. J. Am. Chem. Soc., 2008, 130, 3728-3729.
102. Kano, T.; Takai, J.; Tokuda, O.; Maruoka, K. Design of an axially chiral amino acid with a binaphthyl backbone as an organocatalyst for a direct asymmetric aldol reaction. Angew. Chem. Int. Ed., 2005, 44, 3055-3057.
103. Kano, T.; Tokuda, O.; Takai, J.; Maruoka, K. Design of a binaphthylbased axially chiral amino acid as an organocatalyst for direct asymmetric aldol reactions. Chem. Asian J., 2006, 1-2, 210-215.
104. Kano, T.; Tanaka, Y.; Maruoka, K. Asymmetric organocatalytic oxy-michael addition of alcohols to α, β-Unsaturated aldehydes. Tetrahedron, 2007, 63, 8658-8664.
105. Liu, Q.-Z.; Wang, X.; Luo, S.; Zheng, B.; Qin, D. Facile preparation of optically pure diamines and their applications in asymmetric aldol reactions. Tetrahedron Lett., 2008, 49, 7434-7437.
106. Matsui, K.; Takizawa, S.; Sasai, H. Bifunctional organocatalysts for enantioselective aza-morita-baylis-hillman reaction. J. Am. Chem. Soc., 2005, 127, 3680-3681.
107. Page, P.; Farah, M.; Buckley, B.; Blacker, A.; Lacour, J. Novel binaphthalene-amine catalysts for the asymmetric epoxidation of alkenes. Synlett, 2008, 1381-1385.
108. Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, V.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Asymmetric iminium ion catalysiswith a novel bifunctional primary amine thiourea: controlling adjacent quaternary and tertiary stereocenters. Chem. Eur. J., 2009, 15, 7846-7849.
109. Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Organocatalytic asymmetric michael addition of 2, 4-pentandione to nitroolefins. Org. Lett., 2005, 7, 4713-4716.
110. Shi, Y.-L.; Shi, M. Chiral thiourea-phosphine organocatalysts in the asymmetric aza-morita-baylis-hillman reaction. Adv. Synth. Catal., 2007, 349, 2129-2135.
111. Rabalakos, C.; Wulff, W. Enantioselective organocatalytic direct michael addition of nitroalkanes to nitroalkenes promoted by a unique bifunctional DMAP-Thiourea. J. Am. Chem. Soc., 2008, 130, 13524-13525.
112. Peng, F.; Shao, Z.; Fan, B.; Song, H.; Li, G.; Zhang, H. Advances in asymmetric organocatalytic reactions catalyzed by chiral primary amines. J. Org. Chem., 2008, 73, 5202-5205.
113. Jung, S.; Kim, D. Catalytic Enantioselective electrophilic α-Eydrazination of β-Ketoesters using bifunctional organocatalysts. Tetrahedron Lett., 2008, 49, 5527-5530.
114. Kang, Y.; Kim, D. Organocatalytic highly enantio- and diastereoselective mannich reaction of β-Ketoesters with N-Boc-aldimines. J. Org. Chem., 2009, 74, 5734-5737.
115. Shi, M.; Chen, L.-H. Chiral phosphine lewis bases in catalytic, asymmetric Aza-Morita-Baylis-Hillman reaction. Pure Appl. Chem., 2005, 77, 2105-2110.
116. Shi, M.; Ma, G.-N.; Gao, J. Chiral bifunctional organocatalysts in asymmetric Aza-Morita- Baylis- Hillman reactions of ethyl (Arylimino) acetates with methyl vinyl ketone and ethyl vinyl ketone. J. Org. Chem., 2007, 72, 9779-9781.
117. Shi, M. Li, C.-Q. Catalytic, asymmetric Aza-Baylis-Hillman reaction of Nsulfonated imines with 2-Cyclohexen-1-one and 2-Cyclopenten-1-one in the presence of a chiral phosphine lewis base. Tetrahedron: Asymmetry, 2005, 16, 1385-1391.
118. Shi, M.; Chen, L.-H.; Li, C.-Q. Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis- Hillman reaction of N-Sulfonated imines with activated olefins. J. Am. Chem. Soc., 2005, 127, 3790-3800.
119. Garnier, J.; Anstiss, C.; Liu, F. Enantioselective trifunctional organocatalysts for Rate-Enhanced Aza-Morita-Baylis-Hillman reactions at room temperature. Adv. Synth. Catal., 2009, 351, 331-338.
120. Shi, M.; Liu, Y.-H.; Chen, L.-H. Asymmetric catalysis of morita-baylishillman reactions by chiral phosphine lewis bases bearing multiple phenol groups. Chirality, 2007, 19, 124-128.
121. Lei, Z.-Y.; Ma, G.-N.; Shi, M. A fast catalytic asymmetric Aza-Morita- Baylis-Hillman reaction of N-Sulfonated imines with methyl vinyl ketone in the presence of chiral bifunctional phosphane lewis bases. Eur. J. Org. Chem., 2008, 3817-3820.
122. Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. Chiral phosphine-catalyzed enantioselective construction of γ-Butenolides through substitution of Morita- Baylis- Hillman acetates with 2-Trimethylsilyloxy furan. J. Am. Chem. Soc., 2008, 130, 7202-7203.
123. Sumi, K.; Ikariya, T.; Noyori, R. Efficient synthesis of optically active 2- Amino-2'-diphenylphosphino-1,1'- binaphthyl and its derivatives. Canadian J. Chem., 2000, 78, 697-703.
124. Guan, X.-Y.; Jiang, Y.-Q.; Shi, M. Chiral sterically congested phosphaneamide bifunctional organocatalysts in asymmetric Aza-Morita-Baylis- Hillman reactions of N-Sulfonated imines with methyl and ethyl vinyl ketones. Eur. J. Org. Chem., 2008, 2150-2155.
125. Liu, Y.-H; Shi, M. Dendritic chiral phosphine lewis bases-catalyzed asymmetric Aza-Morita-Baylis-Hillman reaction of N-Sulfonated imines with activated olefins. Adv. Synth. Catal., 2008, 350, 122-128.
126. Qi, M.; Ai, T.; Shi, M.; Li, G. Asymmetric Catalytic aza-Morita-Baylis- Hillman Reaction Using Chiral Bifunctional Phosphine Amides as Catalysts. Tetrahedron, 2008, 64, 1181-1186.
127. Lei, Z.-Y.; Liu, X.-G.; Shi, M.; Zhao, M. Bifunctional chiral phosphinecontaining lewis base catalyzed asymmetric Morita-Baylis-Hillman reaction of aldehydes with activated alkenes. Tetrahedron: Asymmetry, 2008, 19, 2058-2062.
128. Matsui, K.; Takizawa, S.; Sasai, H. Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction. J. Am. Chem. Soc., 2005, 127, 3680-3681.
129. Matsui, K.; Takizawa, S.; Sasai, H. A brønsted acid and lewis base organocatalyst for the Aza-Morita-Baylis- Hillman reaction. Synlett, 2006, 761-765.
130. Matsui, K.; Tanaka, K.; Horii, A.; Takizawa, S.; Sasai, H. Conformational lock in a brønsted acid-lewis base organocatalyst for the aza-Morita-Baylis-Hillman reaction. Tetrahedron: Asymmetry, 2006, 17, 578-583.
131. Sasai, H.; Takizawa, S.; Matsui, K. Patent No.: US 7351835 B2, 2008.
132. Zhou, Y.; Shan, Z. Chiral spiroborate esters catalyzed highly enantioselective direct aldol reaction. Tetrahedron, 2006, 62, 5692-5696.
133. Chu Y.; Shan Z.; Liu, D.; Sun, N. Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework J. Org. Chem., 2006, 71, 3998-4001.
134. Hatano, M.; Ikeno, T.; Miyamoto, T.; Ishihara, K. Chiral lithium binaphtholate aqua complex as a highly effective asymmetric catalyst for cyanohydrin syntesis. J. Am. Chem. Soc., 2005, 127, 10776-10777.
135. Orito, Y.; Hashimoto, S.; Ishizuka, T.; Nakajima, M. Chiral base-catalyzed aldol reaction of trimethoxysilyl enol ethers: effect of water as an additive on stereoselectivities. Tetrahedron, 2006, 62, 390-400.
136. Hatano, M.; Horibe, T.; Ishihara, K. Chiral Lithium(I) binaphtholate salts for the enantioselective direct mannich-type reaction with a change of Syn/Anti and absolute stereochemistry. J. Am. Chem. Soc., 2010, 132, 56-57.