Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 48, 2010, Pages 20666-20671

  Filloux, Claire M ^a   Lathrop, Stephen P ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Catalysis; Organic; Synthesis; Tandem catalysis

Indexed keywords

ALKYNE; SALICYLALDEHYDE;

CATALYSIS; CHEMICAL STRUCTURE; CONFERENCE PAPER; ELECTROPHILICITY; ENANTIOSELECTIVITY; GEOMETRY; MICHAEL ADDITION; PRIORITY JOURNAL; REACTOR CASCADE; SYNTHESIS;

EID: 78650584726     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1002830107     Document Type: Article

References (60)

1. Ajamian A, Gleason JL (2004) Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations. Angew Chem Int Edit 43(29):3754-3760.
2. Lee JM, Na Y, Han H, Chang S (2004) Cooperative multi-catalyst systems for one-pot organic transformations. Chem Soc Rev 33(5):302-312.
3. Wasilke JC, Obrey SJ, Baker RT, Bazan GC (2005) Concurrent tandem catalysis. Chem Rev 105(3):1001-1020.
4. Chapman CJ, Frost CG (2007) Tandem and domino catalytic strategies for enantioselective synthesis. Synthesis(1):1-21.
5. Enders D, Grondal C, Huttl MRM (2007) Asymmetric organocatalytic domino reactions. Angew Chem Int Edit 46(10):1570-1581.
6. Walji AM, MacMillan DWC (2007) Strategies to bypass the taxol problem. Enantioselective cascade catalysis, a new approach for the efficient construction of molecular complexity. Synlett(10):1477-1489.
7. Yu X, Wang W (2008) Organocatalysis: Asymmetric cascade reactions catalysed by chiral secondary amines. Org Biomol Chem 6(12):2037-2046.
8. Alba AN, Companyo X, Viciano M, Rios R (2009) Organocatalytic domino reactions. Curr Org Chem 13(14):1432-1474.
9. Jiang H, et al. (2009) Achieving molecular complexity by organocatalytic one-pot strategies-A fast entry for synthesis of sphingoids, amino sugars, and polyhydroxylated a-amino acids. Angew Chem Int Edit 48(37):6844-6848.
10. Bertelsen S, Jørgensen KA (2009) Organocatalysis-after the gold rush. Chem Soc Rev 38(8):2178-2189.
11. Zhou J (2010) Recent advances in multicatalyst promoted asymmetric tandem reactions. Chem-Asian J 5(3):422-434.
12. Enders D, Huttl MRM, Grondal C, Raabe G (2006) Control of four stereocentres in a triple cascade organocatalytic reaction. Nature 441(7095):861-863.
13. MarigoM, Bertelsen S, Landa A, Jørgensen KA (2006) One-pot organocatalytic domino Michael-Aldol and intramolecular SN2 reactions. Asymmetric synthesis of highly functionalized epoxycyclohexanone derivatives. J Am Chem Soc 128(16):5475-5479.
14. Enders D, Narine AA, Benninghaus TR, Raabe G (2007) Asymmetric organocatalytic domino reactions of γ-nitroketones and enals. Synlett(11):1667-1670.
15. Wang J, et al. (2007) Organocatalytic enantioselective cascade Michael-Aldol condensation reactions: Efficient assembly of densely functionalized chiral cyclopentenes. Angew Chem Int Edit 46(47):9050-9053.
16. Zu L, et al. (2007) Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions. Angew Chem Int Edit 46(20):3732-3734.
17. Hayashi Y, Toyoshima M, Gotoh H, Ishikawa H (2008) Diphenylprolinol silyl ether catalysis in an asymmetric formal carbo [3 + 3] cycloaddition reaction via a domino Michael/Knoevenagel condensation. Org Lett 11(1):45-48.
18. Ishikawa H, Suzuki T, Hayashi Y (2009) High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations. Angew Chem Int Edit 48(7):1304-1307.
19. Zu L, Zhang S, Xie H, Wang W (2009) Catalytic asymmetric oxa-Michael, Michael cascade for facile construction of chiral chromans via an aminal intermediate. Org Lett 11(7):1627-1630.
20. Cernak TA, Lambert TH (2009) Multicatalytic synthesis of a-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reaction. J Am Chem Soc 131(9):3124-3125.
21. Licandro E, et al. (2001) Michael addition of chiral Fischer aminocarbene complexes to nitroolefins: Study on the effect of the Michael acceptor structure on diastereoselectivity. Organometallics 20(3):485-496.
22. Dijk EW, et al. (2004) The asymmetric synthesis of (-)-pumiliotoxin C using tandem catalysis. Tetrahedron 60(43):9687-9693.
23. Huang Y, Walji AM, Larsen CH, MacMillan DWC (2005) Enantioselective organocascade catalysis. J Am Chem Soc 127(43):15051-15053.
24. Shekhar S, Trantow B, Leitner A, Hartwig JF (2006) Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products. J Am Chem Soc 128(36):11770-11771.
25. Simmons B, Walji AM, MacMillan DWC (2009) Cycle-specific organocascade catalysis: Application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis. Angew Chem Int Edit 48(24):4349-4353.
26. Wang YG, Kumano T, Kano T, Maruoka K (2009) Organocatalytic approach to enantioselective one-pot synthesis of pyrrolidine, hexahydropyrrolizine, and octahydroindolizine core structures. Org Lett 11(9):2027-2029.
27. Zhou J, List B (2007) Organocatalytic asymmetric reaction cascade to substituted cyclohexylamines. J Am Chem Soc 129(24):7498-7499.
28. Scroggins ST, Chi Y, Fréchet JMJ (2010) Polarity-directed one-pot asymmetric cascade reactions mediated by two catalysts in an aqueous buffer. Angew Chem Int Edit 49 (13):2393-2396.
29. Lathrop SP, Rovis T (2009) Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/n-heterocyclic carbene catalyzed cascade sequence. J Am Chem Soc 131(38):13628-13630.
30. Read de Alaniz J, Rovis T (2009) The catalytic asymmetric intramolecular Stetter reaction. Synlett(8):1189-1207.
31. Karthikeyan K, Perumal PT (2009) Synthesis of highly functionalized spirobenzofuranols and spirobenzofuranones by Baylis-Hillman reaction. Synlett(14):2366-2370.
32. Pirrung MC, Brown WL, Rege S, Laughton P (1991) Total synthesis of (+)-griseofulvin. J Am Chem Soc 113(22):8561-8562.
33. Sheng R, et al. (2009) Design, synthesis and AChE inhibitory activity of indanone and aurone derivatives. Eur J Med Chem 44(1):7-17.
34. Rønnest MH, et al. (2009) Synthesis and structure-activity relationship of griseofulvin analogues as inhibitors of centrosomal clustering in cancer cells. J Med Chem 52(10): 3342-3347.
35. Awale S, et al. (2008) Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrientdeprived condition. Bioorg Med Chem 16(1):181-189.
36. Charrier C, et al. (2009) Synthesis and modeling of new benzofuranone histone deacetylase inhibitors that stimulate tumor suppressor gene expression. J Med Chem 52(9):3112-3115.
37. Gerard B, Sangji S, O'Leary DJ, Porco JA (2006) Enantioselective photocycloaddition mediated by chiral Brønsted acids: Asymmetric synthesis of the rocaglamides. J Am Chem Soc 128(24):7754-7755.
38. Morton JGM, Kwon LD, Freeman JD, Njardarson JT (2009) An Adler-Becker oxidation approach to vinigrol. Tetrahedron Lett 50(15):1684-1686.
39. Katoh T, Ohmori O, Iwasaki K, Inoue M (2002) Synthetic studies on Sch 202596, an antagonist of the galanin receptor subtype GalR1: An efficient synthesis of (+/-)-geodin, the spirocoumaranone part of Sch 202596. Tetrahedron 58(7):1289-1299.
40. Patonay-Péli E, Litkei G, Patonay T (1990) Flavonoids, 42. Anomalous intramolecular conjugate addition: Synthesis of 2-amino-2-benzyl-3(2H) -benzofuranone and related compounds. Synthesis(6):511-514.
41. He J, Zheng J, Liu J, She X, Pan X (2006) N-heterocyclic carbene catalyzed nucleophilic substitution reaction for construction of benzopyrones and benzofuranones. Org Lett 8(20):4637-4640.
42. Kokubo K, Matsumasa K, Nishinaka Y, Miura M, Nomura M (1999) Reaction of 2-hydroxybenzaldehydes with alkynes, alkenes, or allenes via cleavage of the aldehyde C-H bond using a rhodium catalyst system. Bull Chem Soc Jpn 72(2):303-311.
43. Kadnikov DV, Larock RC (2003) Palladium-catalyzed carbonylative annulation of internal alkynes: Synthesis of 3,4-disubstituted coumarins. J Org Chem 68(24):9423-9432.
44. Capuzzi M, Perdicchia D, J?rgensen KA (2008) Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of β-ketoesters. Chem-Eur J 14(1):128-135.
45. Read de Alaniz J, Kerr MS, Moore JL, Rovis T (2008) Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes. J Org Chem 73(6):2033-2040.
46. Kerr MS, Rovis T (2004) Enantioselective synthesis of quaternary stereocenters via a catalytic asymmetric Stetter reaction. J Am Chem Soc 126(29):8876-8877.
47. Moore JL, Kerr MS, Rovis T (2006) Enantioselective formation of quaternary stereocenters using the catalytic intramolecular Stetter reaction. Tetrahedron 62(49): 11477-11482.
48. Fan MJ, Li GQ, Li LH, Yang SD, Liang YM (2006) DABCO-catalyzed reaction of phenols or 1,2-diphenols with activated alkynes leading to the formation of alkenoic acid esters or 1,3-dioxole derivatives. Synthesis(14):2286-2292.
49. Fan MJ, Li GQ, Liang YM (2006) DABCO catalyzed reaction of various nucleophiles with activated alkynes leading to the formation of alkenoic acid esters, 1,4-dioxane, morpholine, and piperazinone derivatives. Tetrahedron 62(29):6782-6791.
50. DiRocco DA, Oberg KM, Dalton DM, Rovis T (2009) Catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes with nitroalkenes: Backbone fluorination improves selectivity. J Am Chem Soc 131(31):10872-10874.
51. Liu Q, Perreault S, Rovis T (2008) Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates. J Am Chem Soc 130(43):14066-14067.
52. Nair V, Bindu S, Sreekumar V, Rath NP (2003) Unprecedented reactivity of N-heterocyclic carbenes toward DMAD and aldehydes leading to novel multicomponent reactions. Org Lett 5(5):665-667.
53. Nair V, Sreekumar V, Bindu S, Suresh E (2005) Two unprecedented multicomponent reactions involving N-heterocyclic carbenes, activated acetylenes, and aldehydes. Org Lett 7(12):2297-2300.
54. Campbell MJ, Johnson JS (2009) Asymmetric synthesis of (+)-polyanthellin A. J Am Chem Soc 131(30):10370-10371.
55. Chen K, Baran PS (2009) Total synthesis of eudesmane terpenes by site-selective C-H oxidations. Nature 459(7248):824-828.
56. Peelen TJ, Chi Y, Gellman SH (2005) Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: Cocatalyst effects and evidence for an enamine intermediate. J Am Chem Soc 127(33):11598-11599.
57. Dakin HD (1909) The oxidation of hydroxy derivatives of benzaldehyde, acetophenone and related substances. Am Chem J 42(6):477-498.
58. Dakin HD (1910) Oxidation of hydroxy derivatives of benzaldehyde and acetophenone. Proc Chem Soc 25:194.
59. Shi YL, Shi M (2005) DABCO-catalyzed reaction of allenic esters and ketones with salicyl N-tosylimines: Synthesis of highly functionalized chromenes. Org Lett 7(14): 3057-3060.
60. Gupta RK, George MV (1975) Reactions of dimethyl acetylenedicarboxylate- X. Reaction with salicylaldehyde, ortho hydroxyacetophenone, 2-hydroxychalcones and 2,2'-dihydroxychalcones. Tetrahedron 31(10):1263-1275.