New reactions exploring the chemical spaces of the aldol addition of active methylene compounds

Synlett

Volumn , Issue 4, 2012, Pages 524-530

  Massa, Antonio ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

active methylene compounds; aldol addition; multicomponent reactions; tandem aldol addition cyclization

Indexed keywords

CARBENE;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; SYNTHESIS;

EID: 84857452087     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289524     Document Type: Article

References (61)

1. Kirkpatrick P, Ellis C, Nature 2004 432 823
2. Organic and inorganic substances registered by CAS have just exceeded 63 million (www.cas.org).
3. Irwin J J., Nat. Chem. Biol. 2009 5 536
4. Shoichet B K., Nature 2004 432 862
5. Burke M D., Schreiber S L., Angew. Chem. Int. Ed. 2004 43 46
6. A conceptually related approach has recently been reported for the multidimensional reaction screening of ortho -alkynyl benzaldehydes with a variety of catalysts and reaction partners in order to identify new chemical reactions:, Beeler A B., Su S, Singleton C A., Porco J A. Jr., J. Am. Chem. Soc. 2007 129 1413
7. The failure of a planned aldol addition of substituted cyclohexane-1,3-dione in the total synthesis of coleophomones is described here:, Nicolaou K C., Montagnon T, Vassilikogiannakis G, Mathison C J. N., J. Am. Chem. Soc. 2005 127 8872
8. For aldol additions of malonates in the total synthesis of epolactaene, see:, Marumoto S, Kogen H, Naruto S, J. Org. Chem. 1998 63 2068
9. For aldol additions of malonates in the total synthesis of carbohydrates, see:, Saba A, Adovasio V, Nardelli M, Tetrahedron: Asymmetry 1992 3 1573
10. For the preparation of polyfunctional furanic derivatives from trioses, see:, SanchezBallesteros J, McPhee D J., HernandezHernandez F, Rev. Roum. Chem. 1981 26 899
11. For recent studies about catalyst-free aldol additions of 1,3-dicarbonyl compounds to activated aldehydes, see:, Rohra K, Mahrwald R, Adv. Synth. Catal. 2008 350 2877; and references therein
12. For hydroxymethylation of 3-benzoyl-2-oxo-ethylpropionate, see:, Couquelet J, Boyer J B., Coquelet J, Compt. Rend. S. Acad. Sciences, Ser. C: Sciences Chim. 1972 274 422
13. For the hydroxymethylation of 2-oxocyclohexane- and 2- oxocyclo-pentanecarboxylic acid esters in the presence of CaO, see:, Gerdes H, Marschall H, Weyerstahl P, Chem. Ber. 1975 108 3448
14. For the hydroxy-methylation of malonates, see:, Guzaev A, Lönnberg H, Synthesis 1997 1281
15. For the hydroxymethylation of -methyl-substituted acetoacetic ethyl ester, see:, Akeboshi T, Ohtsuka Y, Sugai T, Ohta H, Tetrahedron 1998 54 7387
16. For iron-catalyzed hydroxymethylation, see:, Ogawa C, Kobayashi S, Chem. Lett. 2007 36 56
17. For aldol addition of formaldehyde to 1,3-dicarbonyl compounds used in the total syntheses of natural products, see:, Tsuda Y, Ishiura A, Takamura S, Hosoi S, Isobe K, Mohri K, Chem. Pharm. Bull. 1991 39 2797
18. Chan T H., Schwerdtfeger A E., J. Org. Chem. 1991 56 3294
19. See also some more recent articles: For aldol addition of formaldehyde to activated ketones:, Lecomte V, Bolm C, Adv. Synth. Catal. 2005 347 1666
20. For enantioselective aldol addition of formaldehyde in the presence of chiral palladium complexes:, Fukuchi I, Hamashima Y, Sodeoka M, Adv. Synth. Catal. 2007 349 509
21. For an aldol addition of aqueous formaldehyde with bicyclic -keto ester, see:, Shirakawa S, Shimizu S, Synlett 2007 3160
22. Early attempts in the aldol addition of 1,3-dicarbonyl compounds:, Marvel C S., Stille J K., J. Org. Chem. 1957 22 1451
23. Birkofer L, Ritter A, Vernaleken H, Chem. Ber. 1966 99 2518
24. Wilson B D., J. Org. Chem. 1963 28 314
25. Hellmann H, Dieterich D, Justus Liebigs Ann. Chem. 1962 656 89
26. Mayer R, Gebhardt B, Chem. Ber. 1960 93 1212
27. Schroth W, Treibs W, Justus Liebigs Ann. Chem. 1961 639 214
28. For metallation of malonic esters with calcium in liquid ammonia and their reactivity, see:, Kirilov M, Petrov G, Lazarov A, Izvestiya po Khimiya 1975 8 59
29. Chen W, Pinto B M., Carbohydr. Res. 2007 342 2163
30. For the reaction of chloral, see:, Petrov K A., Tikhonova N A., Lapshina Z Y., Tilkunova N A., Baranov N N., Zh. Org. Khim. 1979 15 265
31. Camps P, Drudis J M., Tetrahedron Lett. 1978 2597
32. Antonioletti R, Bonadies F, Scettri A, J. Org. Chem. 1988 53 5540
33. Umebayashi N, Hamashima Y, Hashizume D, Sodeoka M, Angew. Chem. Int. Ed. 2008 47 4196; Angew. Chem. 2008, 120, 4264
34. Buchanan D J., Dixon D J., Hernandez-Juan F A., Org. Lett. 2004 6 1357
35. Massa A, Scettri A, Filosa R, Capozzolo L, Tetrahedron Lett. 2009 50 7318
36. Massa A, Roscigno A, De Caprariis P, Filosa R, Di Mola A, Adv. Synth. Catal. 2010 352 3348
37. More V, Di Mola A, Perillo M, De Caprariis P, Filosa R, Peduto A, Massa A, Synthesis 2011 3027
38. More V, Di Mola A, Croce G, Tedesco C, Petronzi C, De Caprariis P, Peduto A, Filosa R, Massa A, Org. Biomol. Chem. 2011 9 8483
39. Betson M S., Fleming I, Ouzman J V. A., Org. Biomol. Chem. 2003 1 4017; and references reported therein
40. Denmark S E., Beutner G L., Angew. Chem. Int. Ed. 2008 47 1560
41. Denmark S E., Beutner G L., Winn T, Eastgate M D., J. Am. Chem. Soc. 2005 127 3774
42. Denmark S E., Wynn T, J. Am. Chem. Soc. 2001 123 6199
43. Lee S K., Tambar U K., Perl N R., Leighton J L., Tetrahedron 2010 66 4769
44. Notte G T., Leighton J L., J. Am. Chem. Soc. 2008 130 6676
45. 15a Chiral HPLC separation of 3aa was performed with a Chiralpak AD-H column in hexane-isopropanol (98:2), 0.6 mL/min.
46. Angelin M, Rahm M, Fischer A, Brinck T, Ramström O, J. Org. Chem. 2010 75 5882
47. Selected examples of isoindolinone synthesis: For the synthesis of isoindolinone 9 from o -carboxy benzaldehyde, see:, Rodionov V M., Chukhina E I., Zh. Obshch. Khim. 1944 14 325
48. For the multistep synthesis of isoindolinone 10, see:, Belliotti T R., Brink W A., Kestern S R., Rubin J R., Wistrow D J., Zoski K T., Whetzel S Z., Corbin A E., Pugsley T A., Heffner T G., Wise L D., Bioorg. Med. Chem. Lett. 1998 8 1499
49. Lamblin M, Couture A, Deniau E, Grandclaudon P, Tetrahedron: Asymmetry 2008 19 111
50. Cyclization in the presence of metal catalysts:, Zhu C, Falck J R., Org. Lett. 2011 13 1214
51. For an enantioselective Cu(I)-catalyzed construction of three specific isoindolinones, see:, Guo S, Xie Y, Hu X, Xia C, Huang H, Angew. Chem. Int. Ed. 2010 49 2728
52. Marcelli T, van Maarseveen J H., Hiemstra H, Angew. Chem. Int. Ed. 2006 45 7496
53. Selected examples of isobenzofuranone synthesis:, Mal D, Pahari P, Ranjan De S, Tetrahedron 2007 63 11781
54. Choi P J., Sperry J, Brimble M A., J. Org. Chem. 2010 75 7388
55. Sangshetti J N., Ansari S A. M. K., Shinde D B., Chin. Chem. Lett. 2011 22 163
56. In this context, an interesting enantioselective two-step synthesis of isobenzofuranones in an organocatalyzed aldol reaction of simple ketones or aldehydes to 1d, followed by a lactonization process is:, Zhang H, Zhang S, Liu L, Luo G, Duan W, Wang W, J. Org. Chem. 2010 75 368
57. For selected examples of pyrrolidinone syntheses; see:, Xiao Z.-H, Liu L.-X, Liu C, Huang P.-Q, Synth. Commun. 2011 41 2036
58. Xiang S.-H, Yuan H.-Q, Huang P.-Q, Tetrahedron: Asymmetry 2009 20 2021
59. AlvesJose C F., J. Braz. Chem. Soc. 2007 18 855
60. Matsuo J, Tanaki Y, Ishibashi H, Tetrahedron Lett. 2007 48 3233
61. Lennartz M, Sadakane M, Steckham E, Tetrahedron 1999 55 14407