Meldrum's acids and 5-alkylidene meldrum's acids in catalytic carbon-carbon bond-forming processes

Accounts of Chemical Research

Volumn 43, Issue 3, 2010, Pages 440-454

  Dumas, Aaron M ^a   Fillion, Eric ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DIOXANE DERIVATIVE; MELDRUM ACID; TRANSITION ELEMENT;

ACYLATION; ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ACYLATION; CARBON; CATALYSIS; DIOXANES; STEREOISOMERISM; TRANSITION ELEMENTS;

EID: 77949528712     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar900229z     Document Type: Article

References (73)

1. Meldrum, A. N. A β-Lactonic Acid from Acetone and Malonic Acid. J. Chem. Soc. 1908, 93, 598-601.
2. Davidson, D.; Bernhard, S. A. The Structure of Meldrum's Supposed β-Lactonic Acid. J Am. Chem. Soc. 1948, 70, 3426-3428.
3. For reviews on Meldrum's acid, see:
4. (a) Lipson, V. V.; Gorobets, N. Y. One Hundred Years of Meldrum's Acid: Advances in the Synthesis of Pyridine and Pyrimidine Derivatives. Mol. Diversity 2009, 13, 399-419.
5. (b) Ivanov, A. S. Meldrum's Acid and Related Compounds in the Synthesis of Natural Products and Analogs. Chem. Soc. Rev. 2008, 37, 789-811.
6. (c) Chen, B.C. Meldrum's Acid in Organic Synthesis. Heterocycles 1991, 32, 529-597.
7. Chopra, D.; Zhurov, V. V.; Zhurova, E. A.; Pinkerton, A. A. Chemical Bonding and Structure-Reactivity Correlation in Meldrum's Acid: A Combined Experimental and Theoretical Electron Density Study. J Org. Chem. 2004, 69, 4309-4316.
8. Our group has exploited Meldrum's acids' high acidity, see: Fillion, E.; Wilsily, A.; Fishlock, D. Probing Persistent Intramolecular C-H ⋯ X (X = 0, S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrum's Acid Derivatives. J. Org. Chem. 2009, 74, 1259-1267.
9. Pihlaja, K.; Seilo, M. The Acidity and General Base-Catalyzed Hydrolysis of Meldrum's Acid and Its Methyl Derivatives. Ada Chem. Scand. 1969, 23, 3003-3010.
10. Dauben, W. G.; Kozikowski, A. P.; Zimmerman, W. T. Meldrum's Acid Derivative as a Useful Dienophilic Component: Synthesis of γ-Damascone. Tetrahedron Lett. 1975, 16, 515-517.
11. Mahidol, C.; Pinyopronpanit, Y.; Radviroongit, S.; Thebtaranonth, C.; Thebtaranonth, Y. 1,2-Carbonyl Migration along the Allylic Framework: Synthesis of Alkenylnaphthoquinones. J. Chem. Soc., Chem. Commun. 1988, 1382-1383.
12. For a review, see: Gaber, A. E. M.; McNab, H. Synthetic Applications of the Pyrolysis of Meldrum's Acid Derivatives. Synthesis 2001, 2059-2074.
13. Sato, M.; Ban, H.; Kaneko, C. An Efficient Method for Generation of α-Oxoketenes: Cycloreversion of Enolized Meldrum's Acid Derivatives. Tetrahedron Lett. 1997, 38, 6689-6692.
14. Brown, R. F. C.; Eastwood, F. W.; McMullen, G. L. Methyleneketenes and Methylenecarbenes. VII. Evidence for the Pyrolytic Generation of Methyleneketene (Propadienone). Aust. J Chem. 1977, 30, 179-193.
15. Crow, W. D.; McNab, H. Synthetic Applications of Intramolecular Insertion of Arylcarbenes. III. Generation and Rearrangement of Aryloxycarbenes by Intramolecular Abstraction of Hydrogen. Aust. J. Chem. 1979, 32, 111-121.
16. Swoboda, G.; Swoboda, J.; Wessely, F. Zur Kenntnis Cyclischer Acylale, 8. Mitt. Monatsch Chem. 1964, 95, 1283-1304.
17. NV Reactions. Acc. Chem. Res. 2009, 42, 993-1003.
18. Kunz, F. J.; Polansky, O. E. Organic Lewis Acids. XV. Reaction of Some Substituted Methylene Meldrum's Acids with 2,3-Dimelhylbutadiene. Monatsh. Chem. 1969, 100, 920-927.
19. Rigo, B.; Fasseur, D.; Caulioz, P.; Couturier, D. Reaction of Trimethylsilyl Derivatives with Meldrum's Acid: A New and Easy Monofunctionalization of Malonic Acid. Tetrahedron Lett. 1989, 30, 3073-3076.
20. (a) Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. Meldrum's Acids as Acylating Agents in the Catalytic Intramolecular Friedel-Crafts Reaction. J. Org. Chem. 2005, 70, 1316-1327.
21. 3-Calalyzed Intramolecular Friedel-Crafts Acylation of Benzyl Meldrum's Acids Derivatives. Org. Lett. 2003, 5, 4653-4656.
22. Fillion, E.; Dumas, A. M. Synthesis of Fused 4,5-Disubstituted Indole Ring Systems by Intramolecular Friedel-Crafts Acylation of 4-Substituted Indoles. J. Org. Chem. 2008, 73, 2920-2923.
23. Fillion, E.; Fishlock, D. Metal Triflale-Calalyzed Intramolecular Friedel-Crafts Acylation with Meldrum's Acids - Insights into the Mechanism. Tetrahedron 2009, 65, 6682-6695.
24. For a review on the Lewis acid-induced α-alkylation of carbonyl compounds: Reetz, M. T. Effect of Lewis Acid on the α-Alkylation of Carbonyl Compounds. Angew. Chem., Int. Ed. Engl. 1982, 21, 96-108.
25. Lin, W.-H.; Fang, J.-M.; Cheng, Y.-S. Uncommon Ditorponcs with the Skeleton of Six-Five-Six Fused-Rings from Taiwania cryptomerioides. Phytochemistry 1995, 40, 871-873.
26. Chang, C.-I.; Chang, J.Y.; Kuo, C.-C.; Pan, W.Y.; Kuo, Y.-H. Four New 6-nor5(6→7)Abeo-abielane Type Ditorponcs and Antitumoral Cytotoxic Diterpene Constituents from the bark of Taiwania cryptomerioides. Planta Med. 2005, 71, 72-76.
27. Fillion, E.; Fishlock, D. Total Synthesis of (±)-Taiwaniaquinol B via a Domino Intramolecular Friedel-Crafts Acylation/Carbonyl α-lert-Alkylation Reaction. J. Am. Chem. Soc. 2005, 127, 13144-13145.
28. Kaumanns, O.; Mayr, H. Electrophilicity Parameters of 5-Benzylidene-2,2-Dimctriyl[1,3]dioxane-4,6-diones (Benzylidene Meldrum's Acids). J. Org. Chem. 2008, 73, 2738-2745.
29. Dumas, A. M.; Seed, A.; Zorzitto, A. K.; Fillion, E. A General and Practical Preparation of Alkylidene Meldrum's Acids. Tetrahedron Lett. 2007, 48, 7072-7074.
30. Bigi, F.; Carloni, S.; Ferrari, L; Maggi, R.; Mazzacani, A.; Sartori, G. Clean Synthesis in Water. Part 2: Uncatalyzed Condensation Reaction of Meldrum's Acid and Aldehydes. Tetrahedron Lett. 2001, 42, 5203-5205.
31. Ziegler, F. E.; Guenther, T.; Nelson, R. V. Monoalkylidene Derivatives of Meldrum's Acid. Synth. Commun. 1980, 10, 661-665.
32. Baxter, G. J.; Brown, R. F. C. Melhylenekelenes and Methylenecarbenes. V. Condensation of Ketones with lsopropylidene Malonate Catalyzed by Titanium Tetrachloride and Synthesis of a Dibenzofuran. Aust J. Chem. 1975, 28, 1551-1557.
33. Nair, V. The Reaction of Meldrum's Acid with Aldehydes and Phloroglucinol: A Synthesis of Dihydrocoumarins. Synth. Commun. 1987, 17, 723-727.
34. 3-Catalyzed Reactions of 5-Alkylidene Meldrum's Acids with Phenols: One-Pot Assembly of 3,4-Dihydrocoumarins, 4-Chromanones, Coumarins, and Chromones. J. Org. Chem. 2006, 71, 409-412.
35. Hicken, E. J.; Corey, E. J. Stereoselective Synthesis of Woody Fragrances Related to Georgyone and Arborone. Org. Lett. 2008, 10, 1135-1138.
36. Fillion, E.; Dumas, A. M.; Hogg, S. A. Modular Synthesis of Tetrahydrofluorenones from 5-Alkylidene Meldrum's Acids. J. Org. Chem. 2006, 71, 9899-9902.
37. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Pipko, S. E.; Tolmachev, A. A. Facile One-Pot Synthesis of 1,2,3,4-Tetrahydroquinoline-3- Carboxylic Acids and Their Heterocyclic Analogs. Synth. Commun. 2008, 38, 3032-3043.
38. 3 C-H Bonds and Reactive Alkenyl Oxocarbenium Intermediates. J. Am. Chem. Soc. 2009, 131, 402-403.
39. 3-catalyzed Domino 1,5-Hydride Shift/Cyclization/Friedel-Crafts Acylation Reaction of Benzylidene Meldrum's Acids. Tetrahedron Lett. 2009, 50, 4706-4709.
40. Frost, C. G.; Hartley, B. C. Lewis Base-Promoted Hydrosilylation of Cyclic Malonates: Synthesis of β-Substituted Aldehydes and γ-Substituted Amines. J. Org. Chem. 2009, 74, 3599-3602.
41. Sakai, M.; Hayashi, H.; Miyaura, N. Rhodium-Catalyzed Addition of Aryl- or 1-Alkenylboronic Acids to Enones. Organometallics 1997, 76, 4229-4231.
42. For an overview of Rh-catalyzed conjugate additions, see: Yoshida, K.; Hayashi, T. Rhodium(I)-Catalyzed Asymmetric Addition of Organometallic Reagents to Electron-Deficient Olefins. In Modern Rhodium-Catalyzed Organic Reactions, Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
43. (a) Fillion, E.; Carret, S.; Mercier, L G.; Trepanier, V. É. Sequential Rh(I)/Pd-Catalyzed 1,4-Slereocontrolled Construction of γ-Butyrolactones and Cyclopropanes. Org. Lett. 2008, 10, 437-440.
44. For an asymmetric version, see:
45. (b) Mahonoy, S. J.; Dumas, A. M.; Fillion, E. Asymmetric Addition of Alkenylstannanes to Alkylidene Meldrum's Acids. Org. Lett. 2009, 11, 5346-5349.
46. (a) Shaghafi, M. B.; Kohn, B. L; Jarvo, E. R. Palladium-Catalyzed Conjugate Allylalion Reactions of α,β-Unsaturated N-Acylpyrroles. Org. Lett. 2008, 10, 4743-4746.
47. (b) Sieber, J. D.; Morken, J. P. Asymmetric Ni-Catalyzed Conjugate Allylalion of Activated Enones. J Am. Chem. Soc. 2008, 130, 4978-4983.
48. (c) Shizuka, M.; Snapper, M. L. Catalytic Enantioselective Hosomi-Sakurai Conjugate Allylalion of Cyclic Unsaturated Ketoesters. Angew. Chem., Int. Ed. 2008, 47, 5049-5051.
49. 3-Catalyzed Conjugate Allylalion of Alkylidene Meldrum's Acids. Org. Lett. 2009, 11, 1919-1922.
50. Ramachary, D. B.; Chowdary, 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, 4233-4237.
51. Watanabe, T.; Knöpfel, T. F.; Carreira, E. M. Asymmetric Conjugate Addition Reactions of Meldrum's Acid Derived Acceptors Employing Chiral Phosphoramidite Ligands. Org. Lett. 2003, 5, 4557-4558.
52. Knöpfel, T. F.; Zarotti, P.; Takashi, Y.; Carreira, E. M. Catalytic, Enantioselective, Conjugate Alkyne Addition. J. Am. Chem. Soc. 2005, 127, 9682-9683.
53. For the initial reports of this reaction, which appeared during our studies, see:
54. (a) d'Augustin, M.; Palais, L.; Alexakis, A. Enantioselective Copper-Catalyzed Conjugate Addition to Trisubstituted Cyclohexenones: Construction of Stereogenic Quaternary Centers. Angew. Chem., Int. Ed. 2005, 44, 1376-1378.
55. (b) Wu, J.; Mampreian, D. M.; Hoveyda, A. Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Cu-Catalyzed Asymmetric Conjugate Additions. J. Am. Chem. Soc. 2005, 127, 4584-4585.
56. For recent reviews, see:
57. (a) Thaler, T.; Knochel, P. Copper-Catalyzed Asymmetric Michael Addition of Magnesium, Zinc, and Aluminum Organometallic Reagents: Efficient Synthesis of Chiral Molecules. Angew. Chem., Int. Ed. 2009, 48, 645-648.
58. (b) Jerphagnon, T.; Pizzuti, M. G.; Minnaard, A. J.; Feringa, B. L. Recent Advances in Enantioselective Copper-Catalyzed 1,4-Addition. Chem. Soc. Rev. 2009, 38, 1039-1075.
59. (c) Alexakis, A.; Vuagnoux-d'Augustin, M.; Martin, D.; Kehrli, S.; Palais, L.; Hénon, H.; Hawner, C. Formation of All-Carbon Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition. Chimia 2008, 62, 461-464.
60. Feringa, B. L. Phosphoramidites: Marvelous Ligands in Catalytic Asymmetric Conjugate Addition. Acc. Chem. Res. 2000, 33, 346-353.
61. (a) Wilsily, A.; Fillion, E. Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Conjugate Addition to Alkylidene and Indenylidene Meldrum's Acids. J. Org. Chem. 2009, 74, 8583-8594.
62. (b) Fillion, E.; Wilsily, A. Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Cu-Catalyzed Conjugate Addition of Dialkylzinc Reagents to 5-(1-Arylalkylidene) Meldrum's Acids. J. Am. Chem. Soc. 2006, 128, 2774-2775.
63. Wilsily, A.; Lou, T.; Fillion, E. Enantioselective Copper-Catalyzed Conjugate Addition of Dimethylzinc to 5-(1-Arylalkylidene) Meldrum's Acids. Synthesis 2009, 2066-2072.
64. (a) Hénon, H.; Mauduit, M.; Alexakis, A. Regiodivergent 1,4- versus 1,6-Asymmetric Copper-Catalyzed Conjugate Addition. Angew. Chem., Int. Ed. 2008, 47, 9122-9124.
65. (b) den Hartog, T.; Harutyunyan, S. R.; Font, D.; Minnaard, A. J.; Feringa, B. L. Catalytic Enantioselective 1,6-Conjugate Addition of Grignard Reagents to Linear Dienoates. Angew. Chem., Int. Ed. 2008, 47, 398-401.
66. Fillion, E.; Wilsily, A.; Liao, E.-T. Asymmetric Cu-Catalyzed 1,6-Conjugate Addition of Dialkylzinc Reagents to 5-(3-aryl-2-propenylidene) Meldrum's Acids. Tetrahedron: Asymmetry 2006, 17, 2957-2959.
67. For other examples of asymmetric all-carbon quaternary center formation α to carbonyls, see:
68. (a) Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. All-Carbon Quaternary Stereogenic Centers by Enantioselective Cu-Catalyzed Conjugate Additions Promoted by a Chiral N-Heterocyclic Carbene. Angew. Chem., Int. Ed. 2007, 46, 1097-1100.
69. (b) Shintani, R.; Dua, W.-L.; Hayashi, T. Rhodium-Catalyzed Asymmetric Construction of Quaternary Carbon Stereocenters: Ligand-Dependent Regiocontrol in the 1,4-Addition to Substituted Maleimides. J. Am. Chem. Soc. 2006, 128, 5628-5629.
70. Wilsily, A.; Fillion, E. Asymmetric Synthesis of Carboxylic Acid Derivatives Having an All-Carbon R-Quaternary Center through Cu-Catalyzed 1,4-Addition of Dialkylzinc Reagents to 2-Aryl Acetate Derivatives. Org. Lett. 2008, 10, 2801-2804.
71. Fillion, E.; Zorzitto, A. K. Enantioselective Rhodium-Catalyzed Conjugate Alkynylation of 5-Benzylidene Meldrum's Acid with TMS-Acetylene. J. Am. Chem. Soc. 2009, 131, 14608-14609.
72. For another strategy in Rh(I)-catalyzed additions of silylalkynes see: Nishimura, T.; Guo, X.-X.; Uchiyama, N.; Katoh, T.; Hayashi, T. Steric Tuning Tuning of Silylacetylenes and Chiral Phosphine Ligands for Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of Enones. J. Am. Chem. Soc. 2008, 130, 1576-1577.
73. Wilsily, A.; Nguyen, Y.; Fillion, E. Hydrogenolysis of Unstrained Carbon-Carbon σ Bonds: Stereoselective Entry into Benzylic Tertiary Centers. J. Am. Chem. Soc. 2009, 131, 15606-15607.