Catalytic enantioselective cycloaddition with chiral lewis bases

Current Organic Chemistry

Volumn 15, Issue 24, 2011, Pages 4108-4127

  Lalli, Claudia ^a   Brioche, Julien ^a   Bernadat, Guillaume ^a   Masson, Géraldine ^a  

^a CNRS   (France)

Author keywords

Amine catalysts; Asymmetric; Cycloaddition; Lewis base; Organocatalysis; Phosphine catalysts

Indexed keywords

CATALYSIS; CYCLOADDITION; ENANTIOSELECTIVITY; PHOSPHORUS COMPOUNDS;

AMINE CATALYSTS; ASYMMETRIC; BASE CATALYZED; CYCLOADDITIONS; ENANTIOSELECTIVE CYCLOADDITIONS; ENANTIOSELECTIVE SYNTHESIS; LEWIS BASE; ORGANOCATALYSIS; PHOSPHINE CATALYST; ]+ CATALYST;

CATALYSTS;

EID: 81255197776     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211798109178     Document Type: Article

References (175)

1. Selectivity-A goal for synthetic efficiency; Trost, B. M., Bartmann, W., Eds.; Verlag Chemie: Weinheim, 1984
2. Trost, B. M. Atom Economy-A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way. Angew. Chem. Int. Ed. Eng. 1995, 34, 259
3. Trost, B. The atom economy-- a search for synthetic efficiency. Science 1991, 254, 1471
4. Trost, B. On Inventing Reactions for Atom Economy. Acc. Chem. Res. 2002, 35, 695.
5. Kobayashi, S.; Jørgensen, K. A. Cycloaddition Reactions in Organic Synthesis; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2002, 5
6. Sankararaman, S. Pericyclic Reactions-A Textbook: Reactions, Applications and Theory; Wiley-VCH Verlag GmbH & Co. KgAa: Weinheim, Germany, 2005, 19.
7. Houk, K. N.; Li, Y.; Storer, J.; Raimondi, L.; Beno, B. Concerted and Stepwise Mechanisms in Cycloaddition Reactions: Potential Surfaces and Isotope Effects. J. Chem. Soc., Faraday Trans. 1994, 90, 1599
8. Sankararaman, S.; Pericyclic Reactions-A Textbook, Wiley-VCH: Weinheim, 2005
9. Fleming, I.; Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons: Chichester, 2002.
10. Ishihara, K.; Yamamoto, H. Advances in Catalytic Process; Doyle, M., Ed.; JAI Press: London, United Kingdom, 1995; Vol. 1, pp 29
11. Evans, D. A.; Johnson, J. S. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vol. 3, Chapter 33.1.
12. Bertelsen, S.; Jørgensen, K. A. Organocatalysis-after the gold rush. Chem. Soc. Rev. 2009, 38, 2178
13. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Asymmetric Aminocatalysis-Gold Rush in Organic Chemistry. Angew. Chem., Int. Ed. 2008, 47, 6138
14. Dondoni, A.: Massi, A. Asymmetric Organocatalysis: From Infancy to Adolescence. Angew. Chem., Int. Ed. 2008, 47, 4638
15. Barbas III, C. F. Organocatalysis Lost: Modern Chemistry, Ancient Chemistry, and an Unseen Biosynthetic Apparatus. Angew. Chem., Int. Ed. 2008, 47, 42
16. MacMillan, D. W. C. The Advent and Development of Organocatalysis. Nature, 2008, 455, 304
17. Special issue on asymmetric organocatalysis. Chem. Rev. 2007, 107, 5413
18. Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007
19. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Berkessel, A., Groger, H., MacMillan, D. W. C., Eds.; Wiley-VCH: Weinheim, 2005.
20. Denmark, S. E.; Beutner, G. L. Lewis Base Catalysis in Organic Synthesis. Angew. Chem., Int. Ed. 2008, 47, 1560.
21. Cowen, B. J.; Miller, S. J. Enantioselective catalysis and complexity generation from allenoates. Chem. Soc. Rev. 2009, 38, 3102
22. Paull, D. H., Weatherwax, A.; Lectka, T. Catalytic, asymmetric reactions of ketenes and ketene enolates Review Article. Tetrahedron, 2009, 65, 6771
23. Taggi, A. E.; Hafez, A. M.; Lectka, T. α-Imino Esters: Versatile Substrates for the Catalytic, Asymmetric Synthesis of α- and β-Amino Acids and β-Lactams. Acc. Chem. Res. 2003, 36, 10
24. France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Advances in the Catalytic, Asymmetric Synthesis of β-Lactams. Acc. Chem. Res. 2004, 37, 592.
25. Gaunt, M. J.; Johansson C. C. C. Recent Developments in the Use of Catalytic Asymmetric Ammonium Enolates in Chemical Synthesis. Chem. Rev. 2007, 107, 5596.
26. Marcelli, T.; Hiemstra, H. Cinchona Alkaloids in Asymmetric Organocatalysis. Synthesis 2010, 1229
27. 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.
28. For pioneering works see
29. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels-Alder Reaction. J. Am. Chem. Soc. 2000, 122, 4243
30. Northrup, A. B.; MacMillan, D. W. C. The First General Enantioselective Catalytic Diels-Alder Reaction with Simple α,β- Unsaturated Ketones. J. Am. Chem. Soc. 2002, 124, 2458
31. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. III Organocatalytic Asymmetric Domino Knoevenagel/Diels-Alder Reactions: A Bioorganic Approach to the Diastereospecific and Enantioselective Construction of Highly Substituted Spiro [5,5]undecane-1,5,9-triones. Angew. Chem. Int. Ed. 2003, 42, 4233
32. Gotoh, H.; Hayashi, Y. Diarylprolinol Silyl Ether as Catalyst of an exo- Selective, Enantioselective Diels-Alder Reaction. Org. Lett. 2007, 9, 2859
33. Juhl, K.; Jørgensen, K. A. The First Organocatalytic Enantioselective Inverse-Electron-Demand Hetero-Diels-Alder Reaction. Angew. Chem. Int. Ed. 2003, 42, 1498
34. Han, B.; Li, J.-L.; Ma, C.; Zhang, S.-J.; Chen, Y.-C. Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes. Angew. Chem. Int. Ed. 2008, 47, 9971
35. Han, B.; He, Z.-Q.; Li, J.-L.; Li, R.; Jiang, K.; Liu, T.-Y.; Chen, Y.-C. Organocatalytic Regio- and Stereoselective Inverse- Electron-Demand Aza-Diels-Alder Reaction of α,β-Unsaturated Aldehydes and N-Tosyl-1-aza-1,3-butadienes. Angew. Chem. Int. Ed. 2009, 48, 5474.
36. For a review see: Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Stereoselective Cyclopropanation Reactions. Chem. Rev. 2003, 103, 977.
37. Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Organic-Catalyst-Mediated Cyclopropanation Reaction. Angew Chem. Int. Ed. 2003, 42, 828.
38. Papageorgiou, C. D.; Cubillo de Dios, M.; Ley, S. V.; Gaunt, M. J. Enantioselective Organocatalytic Cyclopropanation via Ammonium Ylides. Angew Chem. Int. Ed. 2004, 43, 4641.
39. Johansson, C. C. C.; Bremeyer, N.; Ley, S. V.; Owen, D. R.; Smith, S. C.; Gaunt, M. J. Enantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid Organocatalysts. Angew Chem. Int. Ed. 2006, 45, 6024.
40. Staudinger, H. Ketene, eine neue Körperklasse. Ber. Dtsch. Chem. Ges. 1905, 38, and 1735
41. Chick, F.; Wilsmore, N. T. M. LXXXIX. Acetylketen: a polymeride of keten. J. Chem. Soc. 1908, 93, 946.
42. Tidwell, T. T. Ketenes, 2nd ed.; John Wiley & Sons: Hoboken, NJ, 2006
43. Tidwell, T. T. The First Century of Ketenes (1905-2005): The Birth of a Versatile Family of Reactive Intermediates. Angew. Chem., Int. Ed. 2005, 44, 5778
44. Orr, R. K.; Calter, M. A. Asymmetric synthesis using ketenes. Tetrahedron 2003, 59, 3545.
45. Ibrahim, A. A.; Harzmann, G. D.; Kerrigan, N. J. Organocatalytic Dimerization of Ketoketenes. J. Org. Chem. 2009, 74, 1777
46. Ibrahim, A. A.; Smith, S. M.; Henson, S.; Kerrigan, N. J. Synthesis of 1,3-diketones through ring-opening of ketoketene dimer β-lactones. Tetrahedron Lett. 2009, 50, 6919.
47. Calter, M. A. Catalytic, Asymmetric Dimerization of Methylketene. J. Org. Chem. 1996, 61, 8006
48. Calter, M. A.; Orr, R. K. Catalytic, Asymmetric Preparation of Ketene Dimers from Acid Chlorides. Org. Lett. 2003, 5, 4745
49. Purohit, V. C.; Richardson, R. D.; Smith, J. W.; Romo, D. Practical, Catalytic, Asymmetric Synthesis of β-Lactones via a Sequential Ketene Dimerization/Hydrogenation Process: Inhibitors of the Thioesterase Domain of Fatty Acid Synthase. J. Org. Chem. 2006, 71, 4549.
50. Calter, M. A.; Guo, X. One-Pot, Catalytic, Asymmetric Syntheses of All Four Stereoisomers of a Dipropionate Synthon. J. Org. Chem. 1998, 63, 5308.
51. For examples of catalytic asymmetric synthesis of β-lactones, see: Schneider, C.; Catalytic, Enantioselective Syntheses of β-Lactones-Versatile Synthetic Building Blocks in Organic Chemistry. Angew. Chem. Int. Ed. 2002, 41, 744.
52. Wynberg, H.; Staring, E. G. J. Asymmetric synthesis of (S)- and (R)- malic acid from ketene and chloral. J. Am. Chem. Soc. 1982, 104, 166
53. Wynberg, H.; Staring, E. G. J. Catalytic asymmetric synthesis of chiral 4- substituted 2-oxetanones. J. Org. Chem. 1985, 50, 1977.
54. Tennyson, R.; Romo, D. Use of In Situ Generated Ketene in the Wynberg β- Lactone Synthesis: New Transformations of the Dichlorinated β-Lactone Products. J. Org. Chem. 2000, 65, 7248.
55. Cortez, G. S.; Tennyson, R. L.; Romo, D. Intramolecular, Nucleophile- Catalyzed Aldol-Lactonization (NCAL) Reactions: Catalytic, Asymmetric Synthesis of Bicyclic β-Lactones. J. Am. Chem. Soc. 2001, 123, 7945.
56. Oh, S. H.; Cortez, G. S.; Romo, D. Asymmetric Synthesis of Bicyclic β- Lactones via the Intramolecular, Nucleophile-Catalyzed Aldol Lactonization: Improved Efficiency and Expanded Scope. J. Org. Chem. 2005, 70, 2835.
57. Wilson, J. E.; Fu, G. C. Asymmetric Synthesis of Highly Substituted β- Lactones by Nucleophile-Catalyzed [2+2] Cycloadditions of Disubstituted Ketenes with Aldehydes. Angew. Chem., Int. Ed. 2004, 43, 6358.
58. Zhu, C.; Shen, X.; Nelson, S. G. Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene-Aldehyde Cycloadditions. J. Am. Chem. Soc. 2004, 126, 5352.
59. Calter, M. A.; Tretyak, O. A.; Flaschenriem, C. Formation of Disubstituted β-Lactones Using Bifunctional Catalysis. Org. Lett. 2005, 7, 1809.
60. Lin, Y.-M.; Boucau, J.; Li, Z.; Casarotto, V.; Lin, J.; Nguyen, A. N.; Ehrmantraut, J. A Lewis Acid-Lewis Base Bifunctional Catalyst from a New Mixed Ligand. Org. Lett. 2007, 9, 567.
61. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. Catalytic, Asymmetric Synthesis of β-Lactams. J. Am. Chem. Soc. 2000, 122, 7831.
62. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of β-Lactams. J. Am. Chem. Soc. 2002, 124, 6626
63. Wack, H.; France, S.; Hafez, A. M.; Drury, W. J., III; Weatherwax, A.; Lectka, T. Development of a New Dimeric Cyclophane Ligand: Application to Enhanced Diastereo- and Enantioselectivity in the Catalytic Synthesis of β-Lactams. J. Org. Chem. 2004, 69, 4531
64. Hafez, A. M.; Dudding, T.; Wagerle, T. R.; Shah, M. H.; Taggi, A. E.; Lectka, T. A Multistage, One-Pot Procedure Mediated by a Single Catalyst: A New Approach to the Catalytic Asymmetric Synthesis of β-Amino Acids. J. Org. Chem. 2003, 68, 5819.
65. France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Bifunctional Asymmetric Catalysis: A Tandem Nucleophile/Lewis Acid Promoted Synthesis of β-Lactams. Org. Lett. 2002, 4, 1603
66. France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. Bifunctional Lewis Acid-Nucleophile-Based Asymmetric Catalysis: Mechanistic Evidence for Imine Activation Working in Tandem with Chiral Enolate Formation in the Synthesis of β-Lactams. J. Am. Chem. Soc. 2005, 127, 1206.
67. Taggi, A. E.; Wack, H.; Hafez, A. M.; France, S.; Lectka, T. Generation of Ketenes from Acid Chlorides Using NaH/Crown Ether Shuttle- Deprotonation for Use in Asymmetric Catalysis. Org. Lett. 2002, 4, 627
68. Shah, M. H.; France, S.; Lectka, T. Bicarbonate Salts as Cost-Effective Bases for the Synthesis of Ketenes and Their Synthetic Equivalents Applied to the Asymmetric Synthesis of β-Lactams. Synlett 2003, 12, 1937
69. Taggi, A. E.; Hafez, A. M.; Dudding, T.; Lectka, T. Molecular mechanics calculations as predictors of enantioselectivity for chiral nucleophile catalyzed reactions. Tetrahedron 2002, 58, 8351
70. Dudding, T.; Hafez, A. M.; Taggi, A. E.; Wagerle, T. R.; Lectka, T. Catalyst that Plays Multiple Roles: Asymmetric Synthesis of β-Substituted Aspartic Acid Derivatives through a Four-Stage, One-Pot Procedure. Org. Lett. 2002, 4, 387.
71. Huang, Y.; Calter, M. A. Catalytic, asymmetric synthesis of α-phenoxy-β- aryl-β-Lactams. Tetrahedron Lett. 2007, 48, 1657.
72. Hodous, B. L.; Fu, G. C. Enantioselective Staudinger Synthesis of β-Lactams Catalyzed by a Planar-Chiral Nucleophile. J. Am. Chem. Soc. 2002, 124, 1578.
73. Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu, G. C. Catalytic Asymmetric Staudinger Reactions to Form β-Lactams: An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent. J. Am. Chem. Soc. 2005, 127, 1 1586.
74. Staudinger, H.; Jelagin, S.; Über Ketene. XV. Einwirkung von Diphenylketen auf Nitrosoverbindungen. Ber. Dtsch. Chem. Ges. 1911, 44, 365.
75. Dochnahl, M.; Fu, G. C. Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives. Angew. Chem. Int. Ed. 2009, 48, 2391.
76. Zwanenburg, B. Sci. Synth. 2004, 27, 123.
77. Koch, F. M.; Peters, R. Catalytic Enantio- and Diastereoselective Formation of β-Sultones: Ring-Strained Precursors for Enantioenriched β- Hydroxysulfonyl Derivatives. Angew. Chem., Int. Ed. 2007, 46, 2685.
78. Koch, F. M.; Peters, R. Rapid Asymmetric Access to β-Hydroxysulfinic Acids and Allylsulfonic Acids by Chemoselective Reduction of β-Sultones. Synlett 2008, 1505.
79. Zajac, M.; Peters, R. Catalytic Asymmetric Formation of β-Sultams. Org. Lett. 2007, 9, 2007.
80. Huisgen, R. 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chem., Int. Ed. Engl. 1963, 10, 565.
81. For recent reviews, see: Pellissier, H. Asymmetric 1,3-dipolar cycloadditions. Tetrahedron 2007, 63, 3235
82. Stanley, L. M.; Sibi, M. P. Enantioselective Copper-Catalyzed 1,3-Dipolar Cycloadditions. Chem. Rev. 2008, 108, 2887
83. Hashimoto, T.; Maruoka, K. In Handbook of Cyclization Reactions; Ma, S., Eds.; Wiley-VCH: Weinheim, Germany, 2009; Chapter 3, p 87 Karlsson, S.
84. Gothelf, K. V.; Jorgensen, K. A. Asymmetric 1,3-Dipolar Cycloaddition Reactions. Chem. Rev. 1998, 98, 863
85. Kanemasa, S. Metal-Assisted Stereocontrol of 1,3-Dipolar Cycloaddition Reactions. Synlett 2002, 1371
86. Broggini, G.; Molteni, G.; Terraneo, A.; Zecchi, G. Transition Metal Complexation in 1,3-Dipolar Cycloadditions. Heterocycles 2003, 59, 823
87. Namboothiri, I. N. N.; Hassner, A. Stereoselective Intramolecular 1,3-Dipolar Cycloadditions Top. Curr. Chem. 2001, 216, 1.
88. For selected examples of chiral phosphoric acid-catalyzed [3+2] cycloadditions, see: Liu, W.-J.; Chen, X.-H.; Gong, L.-Z. Direct Assembly of Aldehydes, Amino Esters, and Anilines into Chiral Imidazolidines via Brønsted Acid Catalyzed Asymmetric 1,3-Dipolar Cycloadditions. Org. Lett. 2008, 10, 5357
89. Yu, J.; He, L.; Chen, X.-H.; Song, J.; Chen, W.-J.; Gong, L.-Z. Highly Enantioselective Catalytic 1,3- Dipolar Cycloaddition Involving 2,3-Allenoates Dipolarophiles. Org. Lett. 2009, 11, 4946.
90. Yu, J.; Chen, W.-J.; Gong, L.-Z. Kinetic Resolution of Racemic 2,3-Allenoates by Organocatalytic Asymmetric 1,3-Dipolar Cycloaddition. Org. Lett. 2010, 12, 4050.
91. Chen, X.-H.; Wei, Q.; Luo, S.- W.; Xiao, H.; Gong, L.-Z. Organocatalytic Synthesis of Spiro [pyrrolidin- 3,3'-oxindoles] with High Enantiopurity and Structural Diversity. J. Am. Chem. Soc. 2009, 131, 13819.
92. Nájera, C.; Sansano, J. M. Azomethine Ylides in Organic Synthesis. Curr. Org. Chem. 2003, 7, 1105
93. Gothelf, K. V. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002; pp 211-245.
94. Alemparte, C.; Blay, G.; Jørgensen, K. A. A Convenient Procedure for the Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes. Org. Lett. 2005, 7, 4569.
95. Agbodjan, A. A.; Cooley, B. E.; Copley, R. C. B.; Corfield, J. A.; Flanagan, R. C.; Glover, B. N.; Guidetti, R.; Haigh, D.; Howes, P. D.; Jackson, M. M.; Matsuoka, R. T.; Medhurst, K. J.; Millar, A.; Sharp, M. J.; Slater, M. J.; Toczko, J. F.; Xie, S.; Asymmetric Synthesis of an NAcylpyrrolidine for Inhibition of HCV Polymerase. J. Org. Chem. 2008, 73, 3094
96. Flanagan, R. C.; Xie, S.; Millar, A. A Catalyzed and Highly Selective Ester Reduction in the Synthesis of an N-Acylpyrrolidine: Safe Design through Reaction Calorimetry and Modeling. Org. Process Res. Develop. 2008, 12, 1307.
97. Xue, M.-X.; Zhang, X.-M.; Gong, L.-Z. The First Organocatalytic Enantioand Diastereoselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with Nitroalkenes. Synlett. 2008, 691.
98. Vakulya, B.; Varga, S.; Csámpai, A.; Soós, T. Highly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts. Org. Lett. 2005, 7, 1967
99. 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, 6367.
100. Xie, J.; Yoshida, K.; Takasu, K.; Takemoto, Y. Thiourea-catalyzed asymmetric formal [3+2] cycloaddition of azomethine ylides with nitroolefins. Tetrahedron Lett. 2008, 49, 6910.
101. Gulevich, A. V.; Zhdanko, A. G., Orru, R. V. A.; Nenajdenko, V. G. Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application. Chem. Rev. 2010, 110, 5235.
102. Schorkopf, U.; Gerhart, F. Carbonyl Olefination with α-Metalated Isocyanides. Angew Chem. Int. Ed. 1968, 7, 805.
103. Schöllkopf, U.; Hantke, K. Synthesen mit α-metallierten Isocyaniden, XXIV. α-Isocyanglutarsäure-diäthylester, Glutaminsäure-Derivate und Pyrrolincarbonsäure-äthylester aus α-metalliertem Isocyanessigsäure- oder - propionsäure-äthylester und Acrylsäureestern. Liebigs Ann. Chem. 1973, 1571.
104. Schöllkopf, U.; Porsch, P.-H. Synthesen mit α-metallierten Isocyaniden, XXV. 4-Cyan-2-isocyanalkansäure-äthylester, 4-Cyan-2- (formylamino)alkansäure-äthylester und 4-Cyan-5(4)-pyrrolin-2- carbonsäure-äthylester aus α-metallierten Isocyanalkansäure-äthylestern und Acrylnitrilen. Chem. Ber. 1973, 106, 3382.
105. Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. Synthetic reactions by complex catalysts. XIX. Copper-catalyzed cycloaddition reactions of isocyanides. Novel synthesis of DELTA.1-pyrroline and. DELTA.2- oxazoline. J. Org. Chem. 1971, 36, 3316.
106. Guo, C.; Xue, M.-X.; Zhu, M.-K.; Gong, L.-Z. Organocatalytic Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoesters to Nitroolefins Leading to Highly Optically Active Dihydropyrroles. Angew Chem. Int. Ed. 2008, 47, 3414.
107. For a seminal work on the Au(I) catalyzed enantioselective aldol reaction between isocyanoesters and carbonyl compound, see: Ito, Y.; Samura, M.; Hayashi, T. Catalytic asymmetric aldol reaction: reaction of aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex. J. Am. Chem. Soc. 1986, 108, 6405.
108. Xue, M.-X.; Guo, C.; Gong, L.-Z. Asymmetric Synthesis of Chiral Oxazolines by Organocatalytic Cyclization of α-Aryl Isocyanoesters with Aldehydes. Synlett 2009, 2191.
109. Zhou, X.-T.; Lin, Y.-R.; Dai, L.-X.; Sun, J.; Xia, L.-J.; Tang, M.-H. A Catalytic Enantioselective Access to Optically Active 2-Imidazoline from NSulfonylimines and Isocyanoacetates. J. Org. Chem. 1999, 64, 1331
110. Zhou, X.-T.; Lin, Y.-R.; Dai, L.-X. A simple and practical access to enantiopure 2,3-diamino acid derivatives. Tetrahedron: Asymmetry 1999, 10, 855
111. Aydin, J.; Rydén, A.; Szabò, K. J. Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate. Tetrahedron: Asymmetry 2008, 19, 1867.
112. Zang, Z.-W.; Lu, G.; Chen, M.-M.; Lin, N.; Li, Y.-B.; Hayashi, T.; Chan, A. S. C. Organocatalytic asymmetric Mannich-type reaction of Nsulfonylimines with isocyanoacetate leading to optically active 2- imidazoline-4-carboxylates. Tetrahedron: Asymmetry 2010, 21, 1715.
113. Li, L.; Ganesh, M.; Seidel, D. Catalytic Enantioselective Synthesis of α,β- Diamino Acid Derivatives. J. Am. Chem. Soc. 2009, 131, 11648.
114. Li, H. M.; 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.
115. Ihara, M.; Fukumoto, K. Syntheses of Polycyclic Natural Products Employing the Intramolecular Double Michael Reaction. Angew Chem. Int. Ed. 1993, 32, 1010.
116. Hoashi, Y.; Yabuta, T.; Takemoto, Y. Bifunctional thiourea-catalyzed enantioselective double Michael reaction of γ,δ-unsaturated β-Ketoester to nitroalkene: asymmetric synthesis of (-)-epibatidine. Tetrahedron Lett. 2004, 45, 9185
117. Hoashi, Y.; Yabuta, T.; Yuan, P.; Miyabe, H.; Takemoto, Y. Enantioselective tandem Michael reaction to nitroalkene catalyzed by bifunctional thiourea: total synthesis of (-)-epibatidine. Tetrahedron 2006, 62, 365.
118. Zu, L.; Xie, H.; Wang, J.; Tang, Y.; Wang, W. Synthesis of Highly Functionalized Chiral Cyclopentanes by Catalytic Enantio- and Diastereoselective Double Michael Addition Reactions. Angew Chem. Int. Ed. 2007, 46, 3732
119. Li, H.; Zu, L.; Xie, H.; Wang, J.; Jiang, W.; Wang, W. Enantioselective Organocatalytic Double Michael Addition Reactions. Org. Lett. 2007, 9, 1833
120. Kang, T.-R.; Xie, J.-W.; Du, W.; Feng, X., Chen, Y.-C. Stereoselective desymmetrisation of prochiral α,α- dicyanoalkenes via domino Michael-Michael addition reactions. Org. Biomol. Chem. 2008, 6, 2673.
121. Tan, B.; Shi, Z.; Chua, P. J.; Zhong, G. Control of Four Stereocenters in an Organocatalytic Domino Double Michael Reaction: Efficient Synthesis of Multisubstituted Cyclopentanes. Org. Lett. 2008, 10, 3425.
122. For a review, see: Peng, F.; Shao, Z. Advances in asymmetric organocatalytic reactions catalyzed by chiral primary amines. J. Mol. Catal. A: Chem. 2008, 285, 1.
123. Enders, D.; Grondal, C.; Hüttl, M. R. M. Asymmetric Organocatalytic Domino Reactions. Angew. Chem. Int. Ed. 2007, 46, 1570.
124. Notz, W.; Tanaka, F.; Barbas, C. F. III 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.
125. Merino, P.; Marquéz-Lopéz, E.; Tejero, T.; Herrera, R. P. Enantioselective Organocatalytic Diels-Alder Reactions. Synthesis 2010, 1.
126. Schreiner, P. R.; Wittkopp, A. H-Bonding Additives Act Like Lewis Acid Catalysts. Org. Lett. 2002, 4, 217
127. Wittkopp, A.; Schreiner, P. R. Metal- Free, Noncovalent Catalysis of Diels-Alder Reactions by Neutral Hydrogen Bond Donors in Organic Solvents and in Water. Chem. Eur. J. 2003, 9, 407.
128. Reviews: Kagan, H. B.; Riant, O. Catalytic asymmetric Diels Alder reactions. Chem. Rev. 1992, 92, 1007
129. Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 3, p 1177
130. Reymond, S.; Cossy, J. Copper-Catalyzed Diels-Alder Reactions. Chem. Rev. 2008, 108, 5359.
131. Bekele, T.; Shah, M. H.; Wolfer, J.; Abraham, C. J.; Weatherwax, A.; Lectka, T. Catalytic, Enantioselective [4 + 2]-Cycloadditions of Ketene Enolates and o-Quinones: Efficient Entry to Chiral, α-Oxygenated Carboxylic Acid Derivatives. J. Am. Chem. Soc. 2006, 128, 1810.
132. Abraham, C. J.; Paull, D. H.; Bekele, T.; Scerba, M. T.; Dudding, T.; Lectka, T. A Surprising Mechanistic "Switch" in Lewis Acid Activation: A Bifunctional, Asymmetric Approach to α-Hydroxy Acid Derivatives. J. Am. Chem. Soc. 2008, 130, 17085.
133. Wolfer, J.; Bekele, T.; Abraham, C. J.; Dogo-Isonagie, C.; Lectka, T. Catalytic, Asymmetric Synthesis of 1, 4-Benzoxazinones: A Remarkably Enantioselective Route to α-Amino Acid Derivatives from o-Benzoquinone Imides. Angew. Chem. Int. Ed. 2006, 45, 7398.
134. Abraham, C. J.; Paull, D. H.; Scerba, M. T.; Grebinski, J. W.; Lectka, T. Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero- Diels-Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides. J. Am. Chem. Soc. 2006, 128, 13370.
135. Xu, X.; Wang, K.; Nelson, S. G. Catalytic Asymmetric [4 + 2] Cycloadditions of Ketenes and N-Thioacyl Imines: Alternatives for Direct Mannich Reactions of Enolizable Imines. J. Am. Chem. Soc. 2007, 129, 11690.
136. Waldmann, H.; Khedkar, V.; Dückert, H.; Schürmann, M.; Oppel, I. M.; Kumar, K. Asymmetric Synthesis of Natural Product Inspired Tricyclic Benzopyrones by an Organocatalyzed Annulation Reaction. Angew. Chem. Int. Ed. 2008, 47, 6869.
137. Riant, O.; Kagan, H. Asymmetric Diels-Alder reaction catalyzed by chiral bases. Tetrahedron Lett. 1989, 30, 7403
138. Riant, O.; Kagan, H. B.; Ricard, L. Asymmetric base-catalyzed cycloaddition between anthrone and some dienophiles. Tetrahedron 1994, 50, 4543.
139. Fache, F.; Piva, O. New perfluoroalkylated cinchona derivatives: synthesis and use in base-catalysed Diels-Alder reactions. Tetrahedron Lett. 2001, 42, 5655.
140. Okamura, H.; Nakamura, Y.; Iwagawa, T.; Nakatami, M. Asymmetric Base- Catalyzed Diels-Alder Reaction of 3-Hydroxy-2-Pyrone with N-Methylmaleimide. Chem. Lett. 1996, 193.
141. Wang, Y.; Li, H.; Wang, Y.-Q.; Liu, Y.; Foxman, B. M.; Deng, L. Asymmetric Diels-Alder Reactions of 2-Pyrones with a Bifunctional Organic Catalyst. J. Am. Chem. Soc. 2007, 129, 6364
142. Singh, R. P.; Bartelson, K.; Wang, Y.; Su, H.; Lu, X.; Deng, L. Enantioselective Diels- Alder Reaction of Simple α,β-Unsaturated Ketones with a Cinchona Alkaloid Catalyst. J. Am. Chem. Soc. 2008, 130, 2422.
143. Goia, C.; Hauville, A.; Bernardi, L.; Fini, F.; Ricci, A. Organocatalytic Asymmetric Diels-Alder Reactions of 3-Vinylindoles. Angew. Chem. Int. Ed. 2008, 47, 9236.
144. Goia, C.; Bernardi, L.; Ricci, A. Asymmetric Diels-Alder Reactions of Vinylindoles Using Organocatalysis. Synthesis 2010, 161.
145. Eitel, M.; Pindur, U. H. Selective Wittig Reactions for the Synthesis of Variously Substituted 2-Vinylindoles. Synthesis 1989, 364
146. Eitel, M.; Pindur, U. H. Reactions of 2-vinylindoles with carbodienophiles: synthetic and mechanistic aspects. J. Org. Chem. 1990, 55, 5368.
147. Hau, C.-K.; He, H.; Lee, A.W.M.; Chik, D. T.W.; Cai, Z.; Wong, H. N.C. Enantioselective Brønsted base catalyzed [4 + 2] cycloaddition using novel amino-substituted tetraphenylene derivatives. Tetrahedron 2010, 66, 9860.
148. For a recent review on chiral phosphine organocatalysts, see: Marinetti, A.; Voituriez, A. Enantioselective Phosphine Organocatalysis. Synlett 2010, 174
149. Ye, L.-W.; Zhou, J.; Tang, Y. Phosphine-triggered synthesis of functionalized cyclic compounds. Chem. Soc. Rev. 2008, 37, 1140
150. Ma, G.-N., J.-J. Jiang, M. Shi, Y. Wei, Recent extensions of the Morita-Baylis- Hillman reaction. Chem. Commun. 2009, 5496.
151. Ibrahim, A. A.; Smith, S. M.; Henson, S.; Kerrigan, N. J. Synthesis of 1,3- diketones through ring-opening of ketoketene dimer β-Lactones. Tetrahedron Lett. 2009, 50, 6919.
152. Ahmad A. Ibrahim, Pei-Hsun Wei, Gero D. Harzmann, and Nessan J. Kerrigan Josiphos-Catalyzed Asymmetric Homodimerization of Ketoketenes. J. Org. Chem. 2010, 75, 7901.
153. Zhang, C.; Lu, X. Phosphine-Catalyzed Cycloaddition of 2,3-Butadienoates or 2-Butynoates with Electron-Deficient Olefins. A Novel [3 + 2] Annulation Approach to Cyclopentenes. J. Org. Chem. 1995, 60, 2906.
154. Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Phosphine triggered [3+2] allenoate-acrylate annulation: a mechanistic enlightenment. Tetrahedron Lett. 2007, 48, 3617
155. Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. An Unexpected Role of a Trace Amount of Water in Catalyzing Proton Transfer in Phosphine- Catalyzed (3 + 2) Cycloaddition of Allenoates and Alkenes. J. Am. Chem. Soc. 2007, 129, 3470
156. Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Mechanism, Regioselectivity, and the Kinetics of Phosphine-Catalyzed [3+2] Cycloaddition Reactions of Allenoates and Electron-Deficient Alkenes. Chem. Eur. J. 2008, 14, 4361.
157. Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao P.; Zhang, X. Asymmetric [3 + 2] Cycloaddition of 2,3-Butadienoates with Electron-Deficient Olefins Catalyzed by Novel Chiral 2,5-Dialkyl-7-phenyl-7- phosphabicyclo [2.2.1]heptanes. J. Am. Chem. Soc. 1997, 119, 3836.
158. Wilson, J. E.; Fu, G. C. Synthesis of Functionalized Cyclopentenes through Catalytic Asymmetric [3+2] Cycloadditions of Allenes with Enones. Angew. Chem. Int. Ed. 2006, 45, 1426.
159. Wallace, D. J.; Sidda, R. L.; Reamer, R. A. Phosphine-Catalyzed Cycloadditions of Allenic Ketones: New Substrates for Nucleophilic Catalysis. J. Org. Chem. 2007, 72, 1051.
160. Voituriez, A.; Panossian, A.; Fleury-Brégeot, N.; Retailleau P.; Marinetti, A. 2-phospha [3]ferrocenophanes with Planar Chirality: Synthesis and Use in Enantioselective Organocatalytic [3 + 2] Cyclizations. J. Am. Chem. Soc. 2008, 130, 14030
161. Voituriez, A.; Panossian, A.; Fleury-Brégeot, N.; Retailleau, P.; Marinetti, A. Synthesis of Chiral 2-Phospha [3]ferrocenophanes and their Behaviour as Organocatalysts in [3+2]Cyclization Reactions. Adv. Synth. Cat. 2009, 351, 1968.
162. Pinto, N.; Neel, M.; Panossian, A.; Retailleau, P.; Frison, G; Voituriez, A.; Marinetti, A. Expanding the Scope of Enantioselective FerroPHANEPromoted [3+2] Annulations with α,β-Unsaturated Ketones. Chem. Eur. J. 2010, 16, 1033.
163. Voituriez, A.; Pinto, N.; Neel, N.; Retailleau, P.; Marinetti, A. An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles. Chem. Eur. J. 2010, 16, 12541.
164. Cowen, B. J.; Miller, S. J. Enantioselective [3+2]-Cycloadditions Catalyzed by a Protected Multifunctional Phosphine-Containing α-Amino Acid. J. Am. Chem. Soc. 2007, 129, 10988.
165. Xaio, H.; Chai, Z.; Zheng, C.-W.; Yang, Y.-Q.; Liu, W.; Zhang, J.-K.; Zhao, G. Asymmetric [3+2] Cycloadditions of Allenoates and Dual Activated Olefins Catalyzed by Simple Bifunctional N-Acyl Aminophosphines. Angew. Chem. Int. Ed. 2010, 49, 4467.
166. Mondal, M.; Ibrahim, A. A.; Wheeler, K. A.; Kerrigan, N. J. Phosphine- Catalyzed Asymmetric Synthesis of β-Lactones from Arylketoketenes and Aromatic Aldehydes. Org. Lett. 2010, 12, 1664.
167. Xu, Z.; Lu, X. A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2- Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin. J. Org. Chem. 1998, 63, 5031
168. Xu, Z.; Lu, X. Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles. Tetrahedron Lett. 1997, 38, 3461.
169. Jean, L.; Marinetti, A. Phosphine-catalyzed enantioselective [3+2] annulations of 2,3-butadienoates with imines. Tetrahedron Lett. 2006, 47, 2141.
170. Fleury-Brégeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Screening of chiral phosphines as catalysts for the enantioselective [3+2] annulations of Ntosylimines with allenic esters. Tetrahedron 2007, 63, 11920.
171. Scherer, A.; Gladysz, J. A. A promising new catalyst family for enantioselective cycloadditions involving allenes and imines: chiral phosphines with transition metal-CH2-P: linkages. Tetrahedron Lett. 2006, 47, 6335.
172. Fang, Y.-Q.; Jacobsen, E. N. Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine-Allene [3+2] Cycloadditions. J. Am. Chem. Soc. 2008, 130, 5660.
173. Zhu, X-F.; Lan, J.; Kwon, O. An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines. J. Am. Chem. Soc. 2003, 125, 4716
174. Tran, Y. S.; Kwon, O. An Application of the Phosphine-Catalyzed [4 + 2] Annulation in Indole Alkaloid Synthesis: Formal Syntheses of (±)-Alstonerine and (±)-Macroline. Org. Lett. 2005, 7, 4289.
175. 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.