Synthesis of 4-hydroxy-4 H -chromenes by reaction of salicylic aldehydes with alkynals catalyzed by silyl prolinol ethers

Synthesis

Volumn , Issue 12, 2011, Pages 1840-1846

  Alemán, José ^a   Alvarado, Cuauhtémoc ^a   Marcos, Vanesa ^a   Núñez, Alberto ^a   Garcíaruano, José Luis ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

aminocatalysis; asymmetric synthesis; chromenes; organocatalysis; proline

Indexed keywords

AMINOCATALYSIS; ASYMMETRIC SYNTHESIS; CHROMENES; ORGANOCATALYSIS; PROLINE;

ALDEHYDES; AMINO ACIDS; CATALYSIS; ETHERS; ORGANIC COMPOUNDS; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

2 (4 TERT BUTYLPHENYL) 4 HYDROXY 4H CHROMENE 3 CARBALDEHYDE; 2 [3,5 BIS(TRIFLUOROMETHYL)PHENYL] 4 HYDROXY 4H CHROMENE 3 CARBALDEHYDE; 2 BUTYL 4 HYDROXY 4H CHROMENE 3 CARBALDEHYDE; 2 CYCLOHEX 1 ENYL HYDROXY 4H CHROMENE 3 CARBALDEHYDE; 4 HYDROXY 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; 4 HYDROXY 4H CHROMENE DERIVATIVE; 4 HYDROXY 6 METHOXY 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; 4 HYDROXY 6 METHYL 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; 4 HYDROXY 6 NITRO 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; 4 HYDROXY 7 METHOXY 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; 4 HYDROXY 8 METHOXY 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; 4,4' OXYBIS(PHENYL 4H CHROMENE 3 CARBALDEHYDE); 6 CHLORO 4 HYDROXY 2 PHENYL 4H CHROMENE 3 CARBALDEHYDE; CHROMENE DERIVATIVE; SALICYLALDEHYDE; SILANE DERIVATIVE; SILYLPROLINOL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENANTIOMER; MICHAEL ADDITION; SOLVENT EFFECT;

EID: 79958081642     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260020     Document Type: Article

References (86)

1. For selected reviews on organocatalysis, see
2. MacMillan D W. C., Nature (London) 2008 455 304
3. Barbas C F. III, Angew. Chem. Int. Ed. 2008 47 42
4. Melchiorre P, Marigo M, Carlone A, Bartoli G, Angew. Chem. Int. Ed. 2008 47 6138
5. Dondoni A, Massi A, Angew. Chem. Int. Ed. 2008 47 4638
6. Erkkil A, Majander I, Pihko P M., Chem. Rev. 2007 107 5416
7. List B, Chem. Commun. 2006 819
8. Nielsen M, Worgull D, Zweifel T, Gschwend B, Bertelsen S, Jrgensen K A., Chem. Commun. 2010 46 611
9. Selected reviews:, Marigo M, Jrgensen K A., Chem. Commun. 2006 2001
10. Guillena G, Ramón D J., Tetrahedron: Asymmetry 2006 17 1465
11. For a general review of -functionalization see:, Tsogoeva S B., Eur. J. Org. Chem. 2007 1701
12. For an excellent book on conjugate additions, see:, Vicario J L., Badía D, Carrillo L, Reyes E, Organocatalytic Enantioselective Conjugate Addition Reactions, RSC Catalysis Series Royal Society of Chemistry Cambridge 2010
13. For a pioneering work, see:, Bertelsen S, Marigo M, Brandes S, Dinér P, Jrgensen K A., J. Am. Chem. Soc. 2006 128 12973
14. Jones S B., Simmons B, MacMillan D W. C., J. Am. Chem. Soc. 2009 131 13606
15. Zhang X, Zhang S, Wang W, Angew. Chem. Int. Ed. 2010 49 1481
16. Alemán J, Núñez A, Marzo L, Marcos V, Alvarado C, GarcíaRuano J L., Chem. Eur. J. 2010 16 9453
17. Liu C, Zhang X, Wang R, Wang W, Org. Lett. 2010 12 4948
18. For a general review of the use of silyl diarylprolinol ethers as catalysts see:, Mielgo A, Palomo C, Chem. Asian J. 2008 3 922
19. Xu L.-W, Li L, Shi Z.-H, Adv. Synth. Catal. 2010 352 243
20. For general reviews on domino, tandem, or multicomponent reactions, see, for example:, Wasilke J.-C, Obrey S J., Baker R T., Bazan G C., Chem. Rev. 2005 105 1001
21. Ramón D J., Yus M, Angew. Chem. Int. Ed. 2005 44 1602
22. Zhu J, Bienaymé H, Multicomponent Reactions Wiley-VCH Weinheim 2005
23. Tietze L F., Brasche G, Gericke K, Domino Reactions in Organic Synthesis Wiley-VCH Weinheim 2006
24. Guo H.-C, Ma J.-A, Angew. Chem. Int. Ed. 2006 45 354
25. Pellissier H, Tetrahedron 2006 62 1619
26. Pellissier H, Tetrahedron 2006 62 2143
27. Yu X, Wang W, Org. Biomol. Chem. 2008 6 2037
28. Grondal C, Jeanty M, Enders D, Nat. Chem. 2010 2 167
29. Zhou J, Chem. Asian J. 2010 5 422
30. For a recent review of the aza-Baylis-Hillman reaction, see
31. Declerck V, Martinez J, Lamaty F, Chem. Rev. 2009 109 1
32. Masson G, Housseman C, Zhu J, Angew. Chem. Int. Ed. 2007 46 4614
33. Shi Y.-L, Shi M, Eur. J. Org. Chem. 2007 2905
34. Krishna P R., Sachwani R, Reddy P S., Synlett 2008 2897
35. Singh V, Batra S, Tetrahedron 2008 64 4511
36. Ma G.-N, Jian J.-J, Shi M, Wei Y, Chem. Commun. 2009 5496
37. There are some examples of the use of chiral secondary amines, mainly proline, for controlling the stereoselectivity, but they require the addition of a tertiary amine as co-catalyst for activation of the double bond. See
38. Imbriglio J E., Vasbinder M M., Miller S J., Org. Lett. 2003 5 3741
39. Chen S H., Hong B C., Su C F., Sarshar S, Tetrahedron Lett. 2005 46 8899
40. Aroyan C E., Vasbinder M M., Miller S J., Org. Lett. 2005 7 3849
41. Nakano A, Kawahara S, Akamatsu S, Morokuma K, Nakatani M, Iwabuchi Y, Takahashi K, Ishihara J, Hatekeyama S, Tetrahedron 2006 62 381
42. Vasbinder M M., Imbriglio J E., Miller S J., Tetrahedron 2006 62 11450
43. Utsumi N, Zhang H, Tanaka F, Barbas C F. III., Angew. Chem. Int. Ed. 2007 46 1878
44. Vesely J, Dziedzic P, Córdova A, Tetrahedron Lett. 2007 48 6900
45. For activation of alkynes in the Baylis-Hillman reaction, see:, Génisson Y, Massardier C, Gautier-Luneau I, Greene A E., J. Chem. Soc., Perkin Trans. 1 1996 2869
46. Sergeeva N N., Golubev A S., Hennig L, Findeisen M, Paetzold E, Oehme G, Burger K, J. Fluorine Chem. 2001 111 41
47. Zhao G.-L, Shi M, J. Org. Chem. 2005 70 9975
48. Li Q, Shi M, Lyte J M., Li G, Tetrahedron Lett. 2006 47 7699
49. For recent references and related compounds see for example:, Labrie F, WO 2010145010 2010
50. Piccagli L, Borgatti M, Nicolis E, Bianchi N, Mancini I, Lampronti I, Vevaldi D, DallAcqua F, Cabrini G, Gambari R, Bioorg. Med. Chem. 2010 18 8341
51. Hosokawa S, Matsushita K, Tokimatsu S, Toriumi T, Suzuki Y, Tatsuta K, Tetrahedron Lett. 2010 51 5532
52. Hai X, Lu X, Zheng P, Liu L, Han C, Hu J, Liu Z, Ma T, Li Y, Wang L, Chen Z, Liu G, J. Med. Chem. 2010 53 1397
53. Sahin H, Nieger M, Nising C F., Bräse S, Synlett 2009 3187
54. Ma T, Liu L, Xue H, Li L, Han C, Wang L, Chen Z, Liu G, J. Med. Chem. 2008 51 1432
55. Ho H.-Y, Chem. Commun. 2010 46 466
56. Ciolkowski M, Malecka M, Modranka R, Budzisz E, J. Mol. Struct. 2009 937 139
57. Demyttenaere J, Syngel K V., Markusse A P., Vervisch S, Debenedetti S, DeKimpe N, Tetrahedron 2002 58 2163
58. Das S G., Doshi J M., Tian D F., Addo S N., Srinivasan B, Hermanson D L., Xing C.-G, J. Med. Chem. 2009 52 5937
59. For oxa-2 H -chromenes, see
60. Govender T, Hojabri L, Moghaddam F M., Arvidsson P I., Tetrahedron: Asymmetry 2006 17 1763
61. Li H, Wang J, E-Nunu T, Zu L, Jiang W, Wei S, Wang W, Chem. Commun. 2007 507
62. Sundén H, Ibrahem I, Zhao G L., Eriksson L, Córdova A, Chem. Eur. J. 2007 13 574
63. Luo S P., Li Z B., Wang L P., Guo Y, Xia A B., Xu D Q., Org. Biomol. Chem. 2009 7 4539
64. Li H, Wang J, Xie H X., Zu L S., Jiang W, Duesler E N., Wang W, Org. Lett. 2007 9 965
65. Sundén H, Rios R, Ibrahem I, Zhao G L., Eriksson L, Córdova A, Adv. Synth. Catal. 2007 349 827
66. Wang W, Li H, Wang J, Zu L S., J. Am. Chem. Soc. 2006 128 10354
67. Rios R, Sundén H, Ibrahem I, Zhao G L., Eriksson L, Córdova A, Tetrahedron Lett. 2006 47 8547
68. Zhao G L., Vesely J, Rios R, Ibrahem I, Sundén H, Córdova A, Adv. Synth. Catal. 2008 350 237
69. Hernandez-Torres G, Urbano A, Carreño M C., Colobert F, Org. Lett. 2009 11 4930
70. For recent references, see:, Duda B, Tverdomed S N., Roeschenthaler G.-V, J. Org. Chem. 2011 76 71
71. Sun Y.-W, Guan X.-Y, Shi M, Org. Lett. 2010 12 566
72. Kurishita Y, Kohira T, Ojida A, Hamachi I, J. Am. Chem. Soc. 2010 132 13290
73. Han X.-L, Lu X.-Y, Org. Lett. 2010 12 108
74. Lu L, Wei J, Chen J, Zhang J, Deng H, Shao M, Zhang H, Cao W, Tetrahedron 2009 65 9152
75. Kumar N N. B., Reddy M N., Swamy K C. K., J. Org. Chem. 2009 74 5395
76. Goto H, Terao Y, Akai S, Chem. Pharm. Bull. 2009 57 346
77. Gerard E M. C., Bräse S, Chem. Eur. J. 2008 14 8086
78. For a review of the reduction of coumarins, see:, Semeniuchnko V, Groth U, Khilya V, Synthesis 2009 3533
79. Lenta B N., Tantangmo F, Devkota K P., Wansi J D., Chouna J R., Soh R C. F., Neumann B, Stammler H.-G, Tsamo E, Sewald N, J. Nat. Prod. 2009 72 2130
80. Cespedes C L., Achnine L, Lotina-Hennsen B, Salazar J R., Gomez-Garibay F, Calderon J S., Pestic. Biochem. Phys. 2001 69 63
81. Es-Safi N.-E, LeGuerneve C, Ducrot P H., Spectrosc. Lett. 2008 41 41
82. Bennie L, Malan E, Coetzee J, Ferreira D, Phytochemistry 2000 53 785
83. Coetzee J, Malan E, Ferreira D, Tetrahedron 1998 54 9153
84. Gomez-Garibay F, Calderon J S., Quijano L, Tellez O, Olivares M. del S, Rios T, Phytochemistry 1997 46 1285
85. Foo L Y., J. Chem. Soc., Chem. Commun. 1989 1505
86. Zanka A, Org. Process Res. Dev. 2000 4 46