Recent advances in enantioselective synthesis of γ-substituted butenolides via the catalytic asymmetric vinylogous reactions

Current Organic Synthesis

Volumn 10, Issue 5, 2013, Pages 764-785

  Zhang, Qi ^a   Liu, Xiaohua ^a   Feng, Xiaomeng ^a  

^a Sichuan University   (China)

Author keywords

substituted butenolide; Asymmetric synthesis; Chiral Lewis acid catalyst; Enantioselectivity; Organocatalyst; Vinylogous reactions

Indexed keywords

EID: 84888097067     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/15701794113109990059     Document Type: Review

References (89)

1. Sellars, J. D.; Steel, P. G. Advances in the synthesis of aryltetralin lignan lactones. Eur. J. Org. Chem. 2007, 3815-3828.
2. Bermejo, A.; Figadère, B.; Zafra-Polo, M.; Barrachina, I.; Estornell, E.; Cortes, D. Acetogenins from annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat. Prod. Rep. 2005, 22, 269-303.
3. Prassas, I.; Diamandis, E. P. Novel therapeutic applications of cardiac glycosides. Nat. Rev. Drug Discov. 2008, 7, 926-935.
4. Roethle, P. A.; Trauner, D. The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products. Nat. Prod. Rep. 2008, 25, 298-317.
5. Rodriguez, A. D. The natural products chemistry of west indian gorgonian octocorals. Tetrahedron 1995, 51, 4571-4618.
6. Damon, R. E.; Schlessinger, R. H. An efficient and stereospecific total synthesis of dl-protolichesterinic acid. Tetrahedron Lett. 1976, 17, 1561-1564.
7. Herrmann, J. L.; Berger, M. H.; Schlessinger, R. H. A total synthesis of racemic avenaciolide. J. Am. Chem. Soc. 1979, 101, 1544-1549.
8. Hanessian, S.; Murray, P. J.; Sahoo, S. P. A tactically novel alternative to acyclic stereoselection based on the concept of a replicating chiron 1, 5-Cmethyl substitution. Tetrahedron Lett. 1985, 26, 5623-5626.
9. Hanessian; S.; Murray, P. J.; Sahoo, S. P. A tactically novel alternative to acyclic stereoselection based on the concept of a replicating chiron 1, 3-and 1, 4-C-Methyl substitution. Tetrahedron Lett. 1985, 26, 5627-5630.
10. Hanessian, S.; Murray, P. J.; Sahoo, S. P. A tactically novel alternative to acyclic stereoselection based on the concept of a replicating chiron access to 1, 3-polyols. Tetrahedron Lett. 1985, 26, 5631-5634.
11. Avetisyan, A. A.; Dangyan, M. T. The chemistry of β-butenolides. Russ. Chem. Rev. 1977, 46, 643-656. For an approach based on ring-closing metathesis.
12. Bassetti, M.; D'Annibale, A.; Fanfoni, A.; Minissi, F. Synthesis of,-unsaturated 4, 5-disubstituted-lactones via ring-closing metathesis catalyzed by the first-generation grubbs' catalyst. Org. Lett. 2005, 7, 1805-1808. For approaches based on lewis-or brønsted-acid-initiated cyclization.
13. Browne, D. M.; Niyomura, O.; Wirth, T. Catalytic use of selenium electrophiles in cyclizations. Org. Lett. 2007, 9, 3169-3171.
14. Goldsmith, D.; Liotta, D.; Lee, C.; Zima, G., The reaction of,-unsaturated acids with phenylselenenyl chloride: decarboxylative elimination vs phenylselenolactonization. Tetrahedron Lett. 1979, 20, 4801-4804. For methods which rely on the oxidation of furans.
15. Pelter, A.; Rowlands, M. The conversion of furans to 2(3H)-butenolides. Tetrahedron Lett. 1987, 28, 1203-1206.
16. Kuwajima, I.; Urabe, H. Regioselective synthesis of 3-butenolides via oxidation of 2-trimethylsilylfurans. Tetrahedron Lett. 1981, 22, 5191-5194.
17. Machado-Araujo, F. W.; Gore, J. Synthese de-2 butenolides a partir du furfural. Tetrahedron Lett. 1981, 22, 1969-1972. For a metal-mediated carbonylative ring closure.
18. Yoneda, E.; Kaneko, T.; Zhang, S.; Onitsuka, K.; Takahashi, S. Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of-and-lactones. Org. Lett. 2000, 2, 441-443.
19. Camps, P.; Cardellach, J.; Corbera, J.; Font, J.; Ortuno, R. M.; Ponsati, O. Studies on structurally simple,-butenolides. III.: Behaviour of (-)-(S)--heterosubstituted-methyl-,-butenolides towards nucleophiles. Protoanemonin as intermediate in an eliminate in an eliminati. Tetrahedron 1983, 39, 395-400.
20. Vigneron, J. P.; Blanchard, J. M. Preparation d'alkyl-4-lactones insaturee optiquement pures. Application a la synthese de la (+) tetrahydrocerulenine. Tetrahedron Lett. 1980, 21, 1739-1742.
21. Midland, M. M.; Tramontano, A. The synthesis of naturally occurring 4-alkyl-and 4-alkenyl--lactones using the asymmetric reducing agent B-3-pinanyl-9-borabicyclo[3. 3. 1]nonane. Tetrahedron Lett. 1980, 21, 3549-3552.
22. Mukaiyama, T.; Suzuki, K. Asymmetric addition of acetylide to aliphatic aldehydes. Preparation of optically active 5-octyl-2(5H)-furanone Chem. Lett. 1980, 9, 255-256.
23. Albinati, A.; Bravo, P.; Ganazzoli, F.; Resnati, G.; Viani, F. Synthesis of both enantiomers of optically pure saturated and,-unsaturated-substituted-lactones from chiral sulphoxides. X-ray molecular structure of (3R, 4S)-4-methyl-4-t-butyl-3-(p-tolylthio)butanolide and of (3R, 4S)-4-(cyclohex-1-enyl)-4-methyl-3-(p-tolylthio)butanolide. J. Chem. Soc., Perkin Trans. I 1986, 1405-1415.
24. Solladié, G.; Frechou, C.; Demailly, G.; Greck, C. Reduction of chiral beta-hydroxy sulfoxides: application to the synthesis of both enantiomers of 4-substituted butenolides. J. Org. Chem. 1986, 51, 1912-1914.
25. Hanessian, S.; Hodges, P. J.; Murray, P. J.; Sahoo, S. P. Mild and efficient preparation of-substituted,-unsturated-butyrolactones from epoxides. J. Chem. SOC., Chem. Commun. 1986, 754-755.
26. Fuson, R. C. The principle of vinylogy. Chem. Rev. 1935, 16, 1-27.
27. Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Preparation and some reactions of 2-trimethylsilyloxyfurans. Heterocycles 1976, 4, 1663-1668.
28. Asaoka, M.; Sugimura, N.; Takei, H. The reactions of 2-(trimethylsiloxy)furans with orthocarboxylic esters, acetals, and acylal in the presence of lewis acids. Bull. Chem. Soc. Jpn. 1979, 52, 1953-1956.
29. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Synthesis of 4-ylidenebutenolides from 2-trimethylsiloxyfuran. Tetrahedron Lett. 1981, 22, 4269-4270.
30. Casiraghi, G.; Rassu, G. Furan-, pyrrole-, and thiophene-based siloxydienes for syntheses of densely functionalized homochiral compounds. Synthesis 1995, 607-626.
31. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. Advances in asymmetric synthesis (Ed.; A. Haassner), JAI Press: Stamford, 1998, 3, 113-189.
32. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. The vinylogous aldol addition of heterocyclic silyloxy dienes: application in synthesis. Synlett 1999, 1333-1350.
33. Denmark, S. E.; Heemstra, J. R. Jr.; Beutner, G. L. Catalytic, enantioselective, vinylogous aldol reactions. Angew. Chem. Int. Ed. 2005, 44, 4682-4698.
34. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver. Chem. Rev. 2000, 100, 1929-1972.
35. Bur, S. K.; Martin, S. F. Vinylogous Mannich reactions: selectivity and synthetic utility. Tetrahedron 2001, 57, 3221-3242.
36. Martin, S. F. Evolution of the vinylogous mannich reaction as a key construction for alkaloid synthesis. Acc. Chem. Res. 2002, 35, 895-904.
37. Soriente, A.; De Rosa, M.; Villano, R.; Scettri, A. Recent advances in asymmetric aldol reaction of masked acetoacetic esters promoted by Ti(IV)/BINOL: a new methodology, non-linear effects and autoinduction. Curr. Org. Chem. 2004, 8, 993-1007.
38. Kalesse, M. Recent advances in vinylogous Aldol reactions and their applications in the syntheses of natural products. Top. Curr. Chem. 2005, 244, 43-76.
39. Denmark, S. E.; Heemstra, J. R. Jr.; Beutner, G. L. Catalytic, enantioselective, vinylogous aldol reactions. Angew. Chem. Int. Ed. 2005, 44, 4682-4698.
40. Denmark, S. E.; Heemstra, J. R. Jr. Lewis base activation of lewis acids: catalytic, enantioselective vinylogous Aldol addition reactions. J. Org. Chem. 2007, 72, 5668-5688.
41. Kalesse, M.; Hassfeld, J. Asymmetric Synthesis; Wiley-VCH: Weinheim, 2007, 105.
42. Hosokawa, S.; Tatsuta, K. Asymmetric vinylogous mukaiyama aldol reactions using vinylketene N, O-acetals in total syntheses of natural products. Mini-Rev. Org. Chem. 2008, 5, 1-18.
43. Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. C2-symmetric copper(II) complexes as chiral lewis acids. Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde. J. Am. Chem. Soc. 1999, 121, 669-685.
44. Evans, D. A.; Dunn, T. B.; Kvoernø, L.; Beauchemin, A.; Raymer, B.; Olhava, E. J.; Mulder, J. A.; Juhl, M.; Kagechika, K.; Favor, D. A. Total synthesis of (+)-azaspiracid-1. Part II: Synthesis of the EFGHI-sulfone and completion of the synthesis. Angew. Chem. Int. Ed. 2007, 46, 4698-4703.
45. Evans, D. A.; Kvoernø, L.; Dunn, T. B.; Beauchemin, A.; Raymer, B.; Mulder, J. A.; Olhava, E. J.; Juhl, M.; Kagechika, K.; Favor, D. A. Total synthesis of (+)-azaspiracid-1. An exhibition of the Intricacies of complex molecule synthesis. J. Am. Chem. Soc. 2008, 130, 16295-16309.
46. Szlosek, M.; Figadère, B. Highly enantioselective Aldol reaction with 2-trimethylsilyloxyfuran: The first catalytic asymmetric autoinductive Aldol reaction. Angew. Chem. Int. Ed. 2000, 39, 1799-1801.
47. Onitsuka, S.; Matsuoka, Y.; Irie, R.; Katsuki, T. Highly enantioselective Cr(salen)-catalyzed reaction of 2-(trimethylsilyloxy)furan and Aaldehydes. Effect of alcohol on enantioselectivity. Chem. Lett. 2003, 32, 974-975.
48. Palombi, L.; Acocella, M. R.; Celenta, N.; Massa, A.; Villano, R.; Scettri, A. Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral lewis base system. Tetrahedron: Asymmetry 2006, 17, 3300-3303.
49. Singh, R. P.; Foxman, B. M.; Deng, L. Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt. J. Am. Chem. Soc. 2010, 132, 9558-9560.
50. Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. C2-symmetric copper(II) complexes as chiral lewis acids. Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters. J. Am. Chem. Soc. 1999, 121, 686-699.
51. Frings, M.; Atodiresei, I.; Runsink, J.; Raabe, G.; Bolm, C. Catalyzed vinylogous mukaiyama aldol reactions with controlled enantio-and diastereoselectivities. Chem. Eur. J. 2009, 15, 1566-1569.
52. Frings, M.; Atodiresei, I.; Wang, Y.; Runsink, J.; Raabe, G.; Bolm, C. C1-symmetric aminosulfoximines in copper-catalyzed asymmetric vinylogous mukaiyama aldol reactions. Chem. Eur. J. 2010, 16, 4577-4587.
53. Ube, H.; Shimada, N.; Terada, M. Asymmetric direct vinylogous aldol reaction of furanone derivatives catalyzed by an axially chiral guanidine base. Angew. Chem. Int. Ed. 2010, 49, 1858-1861.
54. Yang, Y.; Zheng, K.; Zhao, J.; Shi, J.; Lin, L.; Liu, X.; Feng, X. Asymmetric direct vinylogous aldol reaction of unactivated-butenolide to aldehydes. J. Org. Chem. 2010, 75, 5382-5384.
55. Luo, J.; Wang, H.; Han X.; Xu, L. W.; Kwiatkowski J.; Huang, K. W.; Lu, Y. The direct asymmetric vinylogous aldol reaction of furanones with-Ketoesters: access to chiral-butenolides and glycerol derivatives. Angew. Chem. Int. Ed. 2011, 50, 1861-1864.
56. Han, X.; Kwiatkowski, J.; Xue, F.; Huang, K. W.; Lu, Y. Asymmetric mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst. Angew. Chem. Int. Ed. 2009, 48, 7604-7607.
57. Martin, S. F.; Lopez, O. Vinylogous Mannich reactions. Catalytic, asymmetric additions of triisopropylsilyloxyfurans to aldimines. Tetrahedron Lett. 1999, 40, 8949-8953.
58. Carswell, E. I.; Snapper, M. L.; Hoveyda, A. H. A highly efficient and practical method for catalytic asymmetric vinylogous mannich (AVM) reactions. Angew. Chem. Int. Ed. 2006, 45, 7230-7233.
59. Mandai, H.; Mandai, K.; Snapper, M. L.; Hoveyda, A. H. Three-component Ag-catalyzed enantioselective vinylogous mannich and aza-diels-alder reactions with alkyl-substituted aldehydes. J. Am. Chem. Soc. 2008, 130, 17961-17969.
60. Weiland, L. C.; Vieira, E. M.; Snapper, M. L.; Hoveyda, A. H. Ag-catalyzed diastereo-and enantioselective vinylogous Mannich reactions of-ketoimine esters. Development of a method and investigation of its mechanism. J. Am. Chem. Soc. 2009, 131, 570-576.
61. González, A. S.; Arrayás, R. G.; Rivero, M. R.; Carretero, J. C. Catalytic asymmetric vinylogous Mannich reaction of N-(2-thienyl)sulfonylimines. Org. Lett. 2008, 10, 4335-4337.
62. Yuan, Z. L.; Jiang, J. J.; Shi, M. The application of chiral phosphine-Schiff base type ligands in silver(I)-catalyzed asymmetric vinylogous Mannich reaction of aldimines with trimethylsiloxyfuran. Tetrahedron 2009, 65, 6001-6007.
63. Deng, H. P.; Wei, Y.; Shi, M. Axially chiral phosphine-oxazoline ligands in silver(I)-catalyzed asymmetric Mannich reaction of aldimines with trimethylsiloxyfuran. Adv. Synth. Catal. 2009, 351, 2897-2902.
64. Akiyama, T.; Honma, Y.; Itoh, J.; Fuchibe, K. Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid. Adv. Synth. Catal. 2008, 350, 399-402.
65. Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. Direct catalytic asymmetric Mannich-type reactions of-butenolides: effectiveness of brønsted acid in chiral metal catalysis. Org. Lett. 2008, 10, 2319-2322.
66. Zhou, L.; Lin, L.; Ji, J.; Xie, M.; Liu, X.; Feng, X. Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated-angelica lactone. Org. Lett. 2011, 13, 3056-3059.
67. Kitajima, H.; Ito, K.; Katsuki, T. A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates. Tetrahedron 1997, 53, 17015.
68. Kitajima, H.; Katsuki, T. Chiral lewis acid promoted asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans. Synlett 1997, 568-570.
69. Nishikori, H.; Ito, K.; Katsuki, T. A short-step synthesis of trans-whisky lactone by an asymmetric Michael reaction. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
70. Otsuka, K.; Zenibayashi, Y.; Itoh, M.; Totsuka, A. Presence and significance of two diasteromers of-methyl--octalactone in aged distilled liquors. Agric. Biol. Chem. 1974, 38, 485-490.
71. Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. A new and highly efficient catalyst for the enantioselective Mukaiyama-Michael reaction between (E)-3-crotonoyl-1, 3-oxazolidin-2-one and 2-trimethylsilyloxyfuran. Tetrahedron 2001, 57, 10203-10212.
72. Yang, H.; Kim, S. Catalytic enantioselective Mukaiyama-Michael reaction of 2-(trimethylsilyloxy)furan with u-phenylsulfonyl enones. Synlett 2008, 555-560.
73. Suga, H.; Kitamura, T.; Kakehi, A.; Baba, T. Asymmetric Michael addition reactions of 2-silyloxyfurans catalyzed by binaphthyldiimine-Ni(II) complexes. Chem. Commun. 2004, 1414.
74. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched-butenolide architecture. J. Am. Chem. Soc. 2003, 125, 1192-1194.
75. Robichaud, J.; Tremblay, F. Formal enantioselective synthesis of (+)-compactin. Org. Lett. 2006, 8, 597-600.
76. Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. Enantioselective organo-cascade catalysis. J. Am. Chem. Soc. 2005, 127, 15051-15053.
77. Zhang Q.; Xiao X.; Lin L. L.; Liu X. H.; Feng X. M. Highly enantioselective synthesis of-substituted butenolides via the vinylogous Mukaiyama-Michael reaction catalyzed by a chiral scandium(III)-N, N-dioxide complex. Org. Biomol. Chem. 2011, 9, 5748-5754.
78. Trost, B. M.; Hitce, J. Direct asymmetric Michael addition to nitroalkenes: Vinylogous nucleophilicity under dinuclear zinc catalysis. J. Am. Chem. Soc. 2009, 131, 4572-4573.
79. Wang, J.; Qi, C.; Ge, Z.; Cheng, T.; Li, R. Efficient direct asymmetric vinylogous Michael addition reactions of-butenolides to chalcones catalyzed by vicinal primary-diamine salts. Chem. Commun. 2010, 46, 2124-2126.
80. Huang, H.; Yu, F.; Jin, Z.; Li, W.; Wu, W.; Liang, X.; Ye, J. Asymmetric vinylogous Michael reaction of,-unsaturated ketones with-butenolide under multifunctional catalysis. Chem. Commun. 2010, 46, 5957-5959.
81. Zhang, Y.; Yu, C.; Ji, Y.; Wang, W. Diastereo-and enantioselective organocatalytic direct conjugate addition of g-butenolide to chalcones. Chem. Asian J. 2010, 5, 1303-1306.
82. Quintard, A.; Lefranc, A.; Alexakis, A. Highly enantioselective direct vinylogous Michael addition of-butenolide to enals. Org. Lett. 2011, 13, 1540-1543.
83. Cho, C. W.; Krische, M. Regio-and stereoselective construction of-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: an organocatalytic allylic alkylation. Angew. Chem. Int. Ed. 2004, 43, 6689-6691.
84. Jiang, Y. Q.; Shi, Y. L.; Shi, M. Chiral phosphine-catalyzed enantioselective construction of-butenolides through substitution of Morita-Baylis-Hillman acetates with 2-trimethylsilyloxy furan. J. Am. Chem. Soc. 2008, 130, 7202-7203.
85. Cui, H. L.; Huang, J. R.; Lei, J.; Wang, Z. F.; Chen, S.; Wu, L.; Chen, Y. C. Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates. Org. Lett. 2010, 12, 720-723.
86. Zhang, W.; Tan, D.; Lee, R.; Tong, G.; Chen, W.; Qi. B.; Huang, K. W.; Tan, C. H.; Jiang, Z. Highly enantio-and diastereoselective reactions of-substituted butenolides through direct vinylogous conjugate additions. Angew. Chem. Int. Ed. 2012, 51, 10069-10073.
87. Jusseau X.; Retailleau P.; Chabaud L.; Guillou C. Catalytic Enantioselective vinylogous Mukaiyama-Michael addition of 2-silyloxyfurans to cyclic unsaturated oxo esters. J. Org. Chem. 2013, 78, 2289-2300.
88. Das U.; Chen Y. R.; Tsai Y. L.; Lin W. Organocatalytic enantioselective direct vinylogous Michael addition of r-substituted butenolides to 3-aroyl acrylates and 1, 2-diaroylethylenes. Chem. Eur. J. 2013, 19, 7713-7717.
89. Kumar V.; Ray B.; Rathi P.; Mukherjee S. Catalytic asymmetric direct vinylogous Michael addition of-aryl-substituted deconjugated butenolides to nitroolefins and Nphenylmaleimide. Synthesis 2013, 45, 1641-1646.