Recent progress in asymmetric Biginelli reaction

Molecular Diversity

Volumn 17, Issue 2, 2013, Pages 389-407

  Heravi, Majid M ^a   Asadi, Shima ^a   Lashkariani, Boshra Malekzadeh ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

3, 4 Dihydropyrimidin 2(1 H) ones; Asymmetric synthesis; Biginelli; Multicomponent reactions (MCRs)

Indexed keywords

AMINE; CALIXARENE; IONIC LIQUID; PHOSPHORIC ACID DERIVATIVE; PROLINE; PROLINE DERIVATIVE; THIOUREA;

ASYMMETRIC SYNTHESIS; BIGINELLI REACTION; CHEMICAL INTERACTION; PRIORITY JOURNAL; REVIEW;

ACETOACETATES; ALDEHYDES; CATALYSIS; PYRIMIDINONES; STEREOISOMERISM; UREA;

EID: 84880698534     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-013-9439-9     Document Type: Review

References (95)

1. Biginelli P (1893) Aldehyde-urea derivatives of aceto and oxaloacetic acids. Gazz Chim Ital 23:360-413
2. Kappe CO (2003) The generation of dihydropyrimidine libraries utilizing Biginelli multicomponent chemistry. QSAR Comb Sci 22:630-645. doi: 10.1002/qsar.200320001
3. Hekmatshoar R, Heidari M, Heravi MM, Baghernejad B (2009) Efficient sodium selenate-catalyzed synthesis of 3,4-dihydro-2(1 H)- pyrimidinones and -thiones under solvent-free conditions. Bull Chem Soc Ethiop 23:141-144
4. 2O: an efficient and eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1 H)-ones. J Korean Chem Soc 53:90-94. doi: 10.5012/jkcs.2009.53.1.090
5. Hekmatshoar R, Heidari M, Heravi MM, Baghernejad B (2011) Mesoporous molecular sieve MCM-41 catalyzed one-pot synthesis of 3,4-dihydro-2(1 H)-pyrimidinones and -thiones under solvent-free conditions. Bull Chem Soc Ethiop 25:309-313
6. Heravi MM, Bakhtiari K, Bamoharram FF (2006) 12-Molybdophosphoric acid: a recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine- 2(1 H)-ones. Catal Commun 7:373-376. doi: 10.1016/j.catcom.2005.12.007
7. Heravi MM, Behbahani FK, Oskooie HA (2008) Ferric perchlorate catalyzed one-pot synthesis of 1,2,3,4-tetrahydro-2-pyrimidinones and -thiones: an expedient protocol for the Biginelli reaction. Chin J Chem 26:2203-2206. doi: 10.1002/cjoc.200890392
8. Heravi MM, Behbahani FK, Zadsirjan V, Oskooie HA (2006) Iron (III) phosphate dihydrate - catalyzed one-pot synthesis of dihydropyrimidinones and thiones: an improved procedure for the Biginelli reaction. Heterocycl Commun 12:369-372
9. Heravi MM, Derikvand F, Bamoharram FF (2005) A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin-2 (1 H)-one using 12-tungstophosphoric acid. J Mol Catal A 242:173-175. doi: 10.1016/j.molcata. 2005.08.009
10. Khaleghi S, Heravi MM, Khosroshahi M, Behbahani FK, Daroogheha Z (2008) A very high yielding and facile alkaline earth metals homogeneous catalysis of Biginelli reaction: an improved protocol. Green Chem Lett Rev 1:133-139. doi: 10.1080/17518250802342527
11. Moghaddas M, Davoodnia A, Heravi MM, Tavakoli-Hoseini N (2012) Sulfonated carbon catalyzed Biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1 H)-ones and -thiones. Chin J Catal 33:706-710. doi: 10.1016/s1872-2067(11)60377-x
12. 3 immobilized in Al-MCM 41: an efficient catalyst system for the Biginelli reaction. Synth Commun 41:826-831. doi: 10.1080/00397911003668596
13. Tajbakhsh M, Mohajerani B, Heravi MM, Ahmadi AN (2005) Natural HEU type zeolite catalyzed Biginelli reaction for the synthesis of 3,4-dihydropyrimidin- 2(1 H) one derivatives. J Mol Catal A 236:216-219. doi: 10.1016/j.molcata.2005. 04.033
14. 2) catalyzed one-pot multi-component synthesis of 3,4-dihydropyrimidin-2(1 H)-ones and -thiones: an efficient method for the Biginelli reaction. Bull Korean Chem Soc 32:656-658. doi: 10.5012/bkcs.2011.32. 2.656
15. Kappe CO (2000) Biologically active dihydropyrimidones of the Biginelli-type - a literature survey. Eur J Med Chem 35:1043-1052. doi: 10.1016/s0223-5234(00)01189-2
16. Kappe CO (2005) Multicomponent reactions. Wiley-VCH, Weinheim
17. Khanina EL, Siliniece G, Ozols J, Duburs G, Kimenis A (1978) Synthesis and pharmacological studies of some 1,2,3,4-tetrahydropyrimidine-5-carboxylic acid derivatives. Khim Farm Zh 12:72-74
18. Kastron VV, Vitolin RO, Khanina EL, Duburs G, Kimenis A (1987) Fluorine-containing derivatives of 1,2,3,4-tetrahydropyrimidine: synthesis and pharmacological activity. Khim Farm Zh 21:948-952
19. Cho H, Ueda M, Shima K, Mizuno A, Hayashimatsu M, Ohnaka Y, Takeuchi Y, Hamaguchi M, Aisaka K (1989) Dihydropyrimidines: novel calcium antagonists with potent and long-lasting vasodilative and anti-hypertensive activity. J Med Chem 32:2399-2406. doi: 10.1021/jm00130a029
20. Atwal KS, Rovnyak GC, Kimball SD, Floyd DM, Moreland S, Swanson BN, Gougoutas JZ, Schwartz J, Smillie KM, Malley MF (1990) Dihydropyrimidine calcium channel blockers. II. 3-Substituted-4-aryl-1,4-dihydro-6-methyl-5- pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines. J Med Chem 33:2629-2635. doi: 10.1021/jm00171a044
21. Atwal KS, Moreland S (1991) Dihydropyrimidine calcium channel blockers 51: bicyclic dihydropyrimidines as potent mimics of dihydropyridines. Bioorg Med Chem Lett 1:291-294. doi: 10.1021/jm00106a048
22. Alajarin R, Vaquero JJ, Alvarez-Builla J, Sunkel C, Priego JG, Gomez-Sal P, Torres R (1994) Imidazo[1,5-a]pyrimidine and benzo[4,5]imidazo[1,2-a] pyrimidine derivatives as calcium antagonists. Bioorg Med Chem 2:323-329. doi: 10.1016/S0968-0896(00)82188-4
23. Schleifer K-J (1999) Stereoselective characterization of the 1,4-dihydropyridine binding site at L-type calcium channels in the resting state and the opened/inactivated state. J Med Chem 42:2204-2211. doi: 10.1021/jm981114c
24. Nagarathnam D, Miao SW, Lagu B, Chiu G, Fang J, Zhang J, Tyagarajan S, Marzabadi MR, Zhang F, Wong WC, Sun W, Tian D, Wetzel JM, Forray C, Chang RSL, Broten TP, Ransom RW, Schorn TW, Chen TB, O'Malley S, Kling P, Schneck K, Bendesky R, Harrell CM, Vyas KP, Gluchowski C (1999) Design and synthesis of novel α 1a adrenoceptor-selective antagonists. 1. Structure-activity relationship in dihydropyrimidinones. J Med Chem 42:4764-4777. doi: 10.1021/jm990200p
25. Murali Dhar TG, Nagarathnam D, Marzabadi MR, Lagu B, Wong WC, Chiu G, Tyagarajan S, Miao SW, Zhang F, Sun W, Tian D, Shen Q, Zhang J, Wetzel JM, Forray C, Chang RSL, Broten TP, Schorn TW, Chen TB, O'Malley S, Ransom R, Schneck K, Bendesky R, Harrell CM, Vyas KP, Zhang K, Gilbert J, Pettibone DJ, Patane MA, Bock MG, Freidinger RM, Gluchowski C (1999) Design and synthesis of novel α 1a adrenoceptor-selective antagonists. 2. Approaches to eliminate opioid agonist metabolites via modification of linker and 4-methoxycarbonyl-4- phenylpiperidine moiety 1,2. J Med Chem 42:4778-4793. doi: 10.1021/jm990201h
26. Lagu B, Tian D, Nagarathnam D, Marzabadi MR, Wong WC, Miao SW, Zhang F, Sun W, Chiu G, Fang J, Forray C, Chang RSL, Ransom RW, Chen TB, O'Malley S, Zhang K, Vyas KP, Gluchowski C (1999) Design and synthesis of novel α 1a adrenoceptor-selective antagonists. 3. Approaches to eliminate opioid agonist metabolites by using substituted phenylpiperazine side chains. J Med Chem 42:4794-4803. doi: 10.1021/jm990202+
27. Wong WC, Sun W, Lagu B, Tian D, Marzabadi MR, Zhang F, Nagarathnam D, Miao SW, Wetzel JM, Peng J, Forray C, Chang RSL, Chen TB, Ransom R, O'Malley S, Broten TP, Kling P, Vyas KP, Zhang K, Gluchowski C (1999) Design and synthesis of novel α 1a adrenoceptor-selective antagonists. 4. Structure-activity relationship in the dihydropyrimidine series. J Med Chem 42:4804-4813. doi: 10.1021/jm9902032
28. Lagu B, Tian D, Chiu G, Nagarathnam D, Fang J, Shen QR, Forray C, Ransom RW, Chang RSL, Vyas KP, Zhang KY, Gluchowski C (2000) Synthesis and evaluation of furo[3,4-d]pyrimidinones as selective α 1a-adrenergic receptor antagonists. Bioorg Med Chem Lett 10:175-178. doi: 10.1016/S0960-894X(99)00653-8
29. Barrow JC, Glass KL, Selnick HG, Freidinger RM, Chang RSL, O'Malley SS, Woyden C (2000) Preparation and evaluation of 1,3-diaminocyclopentane-linked dihydropyrimidinone derivatives as selective α 1a-receptor antagonists. Bioorg Med Chem Lett 10:1917-1920. doi: 10.1016/S0960-894X(00)00374-7
30. Mayer TU, Kapoor TM, Haggarty SJ, King RW, Schreiber SL, Mitchison TJ (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science 286:971-974. doi: 10.1126/science.286.5441.971
31. Deres K, Schröder CH, Paessens A, Goldmann S, Hacker HJ, Weber O, Krämer T, Niewöhner U, Pleiss U, Stoltefuss J, Graef E, Koletzki D, Masantschek RNA, Reimann A, Jaeger R, Groß R, Beckermann B, Schlemmer KH, Haebich D (2003) Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids. Science 299:893-896. doi: 10.1126/science.1077215
32. Heys L, Moore CG, Murphy PJ (2000) The guanidine metabolites of Ptilocaulisspiculifer and related compounds; isolation and synthesis. Chem Soc Rev 29:57-67. doi: 10.1039/A903712H
33. Barluenga J, Tomas M, Rubio V, Gotor VJ (1995) J Chem Soc Chem Commun. pp 1369-1370.
34. Aron ZD, Overman LE (2004) The tethered Biginelli condensation in natural product synthesis. Chem Commun 2004:253-265
35. Kolosov MA, Orlov VD, Beloborodov DA, Dotsenko VV (2009) A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1 H)-ones (-thiones) synthesis. Mol Divers 13:5-25. doi: 10.1007/s11030-008-9094-8
36. Lu J, Bai Y (2002) Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates. One-pot synthesis of 3,4-dihydropyrimidin-2(1 H)-ones. Synthesis 4:466-470. doi: 10.1055/s-2002-20956
37. Varala R, Mujahid AM, Adapa SP (2003) Bismuth triflate catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2 (1 H)-ones: an improved protocol for the Biginelli reaction. Synlett 1:67-70. doi: 10.1055/s-2003-36216
38. 2O. J Braz Chem Soc 15:165-169. doi: 10.1590/S0103-50532004000200002
39. Ranu BC, Hajra A, Jana U (2000) Indium (III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction. J Org Chem 65:6270-6272. doi: 10.1021/jo000711f
40. Maliga Z, Kapoor MT, Mitchison TJ (2002) Evidence that monastrol is an allosteric inhibitor of the mitotic kinesin Eg5. Chem Biol 9:989-996. doi: 10.1016/S1074-5521(02)00212-0
41. DeBonis S, Simorre J-P, Crevel I, Lebeau L, Skoufias DA, Blangy A, Ebel C, Gans P, Cross R, Hackney DD, Wade RH, Kozielski F (2003) Interaction of the mitotic inhibitor Monastrol with human kinesin Eg5. Biochem 42:338-349. doi: 10.1021/bi026716j
42. Barrow JC, Nantermet PG, Selnick HG, Glass KL, Rittle KE, Gilbert KF, Steele TG, Homnick CF, Freidinger RM, Ransom RW, Kling P, Reiss D, Broten TP, Schorn TW, Chang RSL, O'Malley SS, Olah TV, Ellis JD, Barrish A, Kassahun K, Leppert P, Nagarathnam D, Forray C (2000) In vitro and in vivo evaluation of dihydropyrimidinone α -5 amides as potent and selective α 1a receptor antagonists for the treatment of benign prostatic hyperplasia. J Med Chem 43:2703-2718. doi: 10.1021/jm990612y
43. Wisen S, Androsavich J, Evans CG, Chang L, Gestwicki JE (2008) Chemical modulators of heat shock protein 70 (Hsp70) by sequential, microwaveaccelerated reactions on solid phase. Bioorg Med Chem Lett 18:60-65. doi: 10.1016/j.bmcl.2007.11.027
44. Jinwal UK, Miyata Y, Koren JI, Jones JR, Trotter JH, Chang L, O'Leary J, Morgan D, Lee DC, Shults CL, Rousaki A, Weeber EJ, Zuiderweg ERP, Gestwicki JE, Dickey CA (2009) Chemical manipulation of Hsp70 ATPase activity regulates Tau stability. J Neurosci 29:12079-12088. doi: 10.1523/JNEUROSCI.3345-09.2009
45. Fewell SW, Smith CM, Lyon MA, Dumitrescu TP, Wipf P, Day BW, Brodsky JL (2004) Small molecule modulators of endogenous and cochaperone stimulated Hsp70 ATPase activity. J Biol Chem 279:51131-51140. doi: 10.1074/jbc.M404857200
46. Rodina A, Vilenchik M, Moulick K, Aguirre J, Kim J, Chiang A, Litz J, Clement CC, Kang Y, She Y, Wu N, Felts S, Wipf P, Massague J, Jiang X, Brodsky JL, Krystal GW, Chiosis G (2007) Selective compounds define Hsp90 as a major inhibitor of apoptosis in small-cell lung cancer. Nat Chem Biol 3:498-507. doi: 10.1038/nchembio.2007.10
47. Evans CG, Wisen S, Gestwicki JE (2006) Heat Shock Proteins 70 and 90 inhibit early stages of amyloid B-(1-42) aggregation in vitro. J Biol Chem 281:33182-33191. doi: 10.1074/jbc.M606192200
48. Bozsing D, Sohar P, Gigler G, Kovacs G (1996) Synthesis and pharmacological study of new 3,4-dihydro-2 H,6 H -pyrimido-[2,1-b][l,3] thiazines. Eur J Med Chem 31:663-668. doi: 10.1016/0223-5234(96)85874-0
49. Ghorab MM, Mohamed YA, Mohamed SA, Ammar YA (1996) Synthesis and radiation stability of novel thiazolopyrimidines with expected antifungal activity. Phosphorus Sulfur 108:249-256. doi: 10.1080/10426509608029657
50. Ashok M, Holla BS, Kumari NS (2007) Convenient one pot synthesis of some novel derivatives of thiazolo[2,3-b]dihydropyrimidinone possessing 4-methylthiophenyl moiety and evaluation of their antibacterial and antifungal activities. Eur J Med Chem 42:380-385. doi: 10.1016/j.ejmech.2006.09.003
51. Magerramov AM, Kurbanova MM, Abdinbekova RT, Rzaeva IA, Farzaliev VM, Allakhverdiev MA (2006) Synthesis and antioxidative properties of some 3,4-dihydropyrimidin-2(1 H)ones(-thiones). Russ J Appl Chem 79:787-790. doi: 10.1134/S107042720605017X
52. Wichmann J, Adam G, Kolczewski S, Mutel V, Woltering T (1999) Structure-activity relationships of substituted 5 H -thiazolo[3,2-a]pyrimidines as group 2 metabotropic glutamate receptor antagonists. Bioorg Med Chem Lett 9:1573-1576. doi: 10.1016/S0960-894X(99)00227-9
53. Suresh, Sandhu SJ (2012) Past, present and future of the Biginelli reaction: a critical perspective. Arkivoc 1:66-133
54. Matache M, Dobrota C, Bogdan ND, Funeriu DP (2011) Recent developments in the reactivity of the Biginelli compounds. Curr Org Synth 8:356-373. doi: 10.2174/10356
55. de Graaff C, Ruijter E, Orru RVA (2012) Recent developments in asymmetric multicomponent reactions. Chem Soc Rev 41:3969-4009. doi: 10.1039/C2CS15361K
56. Guillena G, Ramón DJ, Yus M (2007) Organocatalytic enantioselective multicomponent reactions (OEMCRs). Tetrahedron Asymmetry 18:693-700. doi: 10.1016/j.tetasy.2007.03.002
57. Gong LZ, Chen XH, Xu XY (2007) Asymmetric organocatalytic Biginelli reactions: a new approach to quickly access optically active 3,4-dihydropyrimidin-2-(1 H)-ones. Chem Eur J 13:8920-8926. doi: 10.1002/chem.200700840
58. Heravi MM, Asadi S (2012) Recent applications of organocatalysts in asymmetric aldol reactions. Tetrahedron Asymmetry 23:1431-1465
59. 5/primary amine catalyzed Biginelli reaction. Eur J Org Chem 2010:4986-4990. doi: 10.1002/ejoc.201000894
60. Ding D, Zhao CG (2010) Primary amine-catalyzed Biginelli reaction for the enantioselective synthesis of 3,4-dihydropyrimidin-2(1 H)-ones. Eur J Org Chem 2010:3802-3805. doi: 10.1002/ejoc.201000448
61. Huang Y, Yang F (2005) Highly enantioseletive Biginelli reaction using a new chiral ytterbium catalyst? asymmetric synthesis of dihydropyrimidines. J Am Chem Soc 127:16386-16387. doi: 10.1021/ja056092f
62. Li N, Chen X-H, Song J, Luo S-W, Fan W, Gong L-Z (2009) Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: reversal of the stereochemistry by tuning the 3,3′ -disubstituents of phosphoric acids. J Am Chem Soc 131:15301-15310. doi: 10.1021/ja905320q
63. Huang Y, Yang F, Zhu C (2005) Highly enantioseletive Biginelli reaction using a new chiral ytterbium catalyst:asymmetric synthesis of dihydropyrimidines. J Am Chem Soc 127:16386-16387. doi: 10.1021/ja056092f
64. Xu D-Z, Li H, Wang Y (2012) Highly enantioselective Biginelli reaction catalyzed by a simple chiral primary amine catalyst: asymmetric synthesis of dihydropyrimidines. Tetrahedron 68:7867-7872. doi: 10.1016/j.tet.2012.07.027
65. Saha S, Moorthy JN (2011) Enantioselective organocatalytic Biginelli reaction: dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality. J Org Chem 76:396-402. doi: 10.1021/jo101717m
66. Sohn JHC, Lee HM, Joung S, Lee SHY (2009) Probing the mode of asymmetric induction of Biginelli reaction using proline ester salts. Eur J Org Chem 2009:3858-3862. doi: 10.1002/ejoc.200900455
67. González-Olvera R, Demare P, Regla I, Juaristi E (2008) Application of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane derivatives in asymmetric organocatalysis: the Biginelli reaction. Arkivoc 2008:61-72
68. Wang YY, Yu J, Miao Z, Chena R (2009) Highly enantioselective Biginelli reaction promoted by chiral bifunctional primary amine-thiourea catalysts: asymmetric synthesis of dihydropyrimidines. Adv Synth Catal 351:3057-3062. doi: 10.1002/adsc.200900597
69. Wang Y, Yu J, Miao Z, Chen R (2011) Bifunctional primary amine-thiourea-TfOH (BPAT · TfOH) as a chiral phase-transfer catalyst: the asymmetric synthesis of dihydropyrimidines. Org Biomol Chem 9:3050-3054. doi: 10.1039/C0OB01268H
70. List B (2006) The ying and yang of asymmetric aminocatalysis. Chem Commun: 819-824. doi: 10.1039/B514296M
71. Zhu M-K, Cun L-F, Mi A-Q, Jiang Y-Z, Gong L-Z (2006) A highly enantioselective organocatalyst for the Michael addition of cyclic ketones to nitroolefins. Tetrahedron: Asymmetry 17:491-493. doi: 10.1016/j.tetasy.2006.01. 034
72. Chowdari NS, Ramachary DB, Barbas CF (2003) Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized β -amino alcohols from aldehydes, ketones, and azodicarboxylates. Org Lett 5:1685-1688. doi: 10.1021/o1034333n
73. Xin J, Chang L, Hou Z, Shang D, Liu X, Feng X (2008) An Enantioselective Biginelli reaction catalyzed by a simple chiral secondary amine and achiral brønsted acid by a dual- activation route. Chem Eur J 14:3177-3181. doi: 10.1002/chem.200701581
74. Chen X-H, Xu X-Y, Liu H, Cun L-F, Gong L-Z (2006) Highly enantioselective organocatalytic Biginelli reaction. J Am Chem Soc 128:14802-14803. doi: 10.1021/ja065267y
75. Li Z-Y, Chen J-W, Liu Y, Xia W, Wang L (2011) The use of calixarenes in asymmetric catalysis. Curr Org Chem 15:39-61. doi: 10.2174/138527211793797837
76. Li ZY, Chen JW, Wang L, Pan Y (2009) Highly enantioselective direct aldol reactions catalyzed by proline derivatives based on a calix[4]arene scaffold in the presence of water. Synlett 2009:2356-2360. doi: 10.1055/s-0029-1217710
77. Li ZY, Lu CX, Huang G, Ma JJ, Sun H, Wang L, Pan Y (2010) Novel prolinamide organocatalysts based on calix[4]arene scaffold for the enantioselective direct aldol reaction. Lett Org Chem 7:461-466. doi: 10.2174/157017810791824919
78. Grekov AP, Veselov VY (1978) The α -effect in the chemistry of organic compounds. Russ Chem Rev 47:631-648. doi: 10.1070/ RC1978v047n07ABEH002243
79. Fina NJ, Edwards JO (1973) The alpha effect. A review. Int J Chem Kinet 5:1-26. doi: 10.1002/kin.550050102
80. Fleming I (1977) Frontier orbitals and organic chemical reactions. Wiley, London
81. Hinman R (1958) Notes-base strengths of some alkylhydrazines. J Org Chem 23:1587-1588. doi: 10.1021/jo01104a629
82. Cavill JL, Peters JU, Tomkinson NCO (2003) Iminium ion catalysis: use of the α -effect in the acceleration of the Diels-Alder reaction. Chem Commun 2003(6):728-729. doi: 10.1039/B212239A
83. Lemay M, Ogilvie WW (2006) Mechanistic studies of hydrazide-catalyzed enantioselective Diels-Alder reactions. J Org Chem 71:4663-4666. doi: 10.1021/jo060339p
84. Lemay M, Ogilvie WW (2005) Aqueous enantioselective organocatalytic Diels-Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration. Org Lett 7:4141-4144. doi: 10.1021/ol051476w
85. Ahn JH, Shin MS, Jun MA, Jung SH, Kang SK, Kim KR, Rhee SD, Kang NS, Kim SY, Sohn S-K, Kim SG, Jin MS, Lee JO, Cheon HG, Kim SS (2007) Synthesis, biological evaluation and structural determination of β -aminoacyl-containing cyclic hydrazine derivatives as dipeptidyl peptidase IV (DPP-IV) inhibitors. Bioorg Med Chem 17:2622-2628. doi: 10.1016/j.bmcl.2007.01. 111
86. Suzuki I, Iwata Y, Takeda K (2008) Biginelli reactions catalyzed by hydrazine type organocatalyst. Tetrahedron Lett 49:3238-3241. doi: 10.1016/j.tetlet.2008.03.080
87. Wu YY, Chai Z, Liu XY, Zhao G, Wang SW (2009) Synthesis of substituted 5-(pyrrolidin-2-yl)tetrazoles and their application in the asymmetric Biginelli reaction. Eur J Org Chem 2009:904-911. doi: 10.1002/ejoc.200801046
88. Rodríguez B, Bolm C (2006) Thermal effects in the organocatalytic asymmetric Mannich reaction. J Org Chem 71:2888-2891. doi: 10.1021/jo060064d
89. Westermann B, Neuhaus C (2005) Dihydroxyacetone in amino acid catalyzed Mannich-type reactions. Angew Chem Int Ed 44:4077-4079. doi: 10.1002/anie.200500297
90. Mossé S, Alexakis A (2006) Organocatalyzed asymmetric reactions via microwave activation. Org Lett 8:3577-3580. doi: 10.1021/ol0614727
91. Hosseini M, Stiasni N, Barbieri V, Kappe CO (2007) Microwave-assisted asymmetric organocatalysis. A probe for nonthermal microwave effects and the concept of simultaneous cooling. J Org Chem 72:1417-1424. doi: 10.1021/jo0624187
92. Yadav LDS, Rai A, Rai VK, Awasthi C (2008) Chiral ionic liquid-catalyzed Biginelli reaction: stereoselective synthesis of polyfunctionalized perhydropyrimidines. Tetrahedron 64:1420-1429. doi: 10.1016/j.tet.2007.11.044
93. Tao G-H, He L, Sun N, Kou Y (2005) New generation ionic liquids: Cations derived from amino acids. Chem Commun 2005:3562-3564. doi: 10.1039/b504256a
94. Li N, Chen X-H, Song J, Luo S-W, Fan W, Gong L-Z (2009) Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: reversal of the stereochemistry by tuning the 3,3 ′ -disubstituents of phosphoric acids. J Am Chem Soc 131:15301-15310. doi: 10.1021/ja905320q
95. Goss JM, Schaus SE (2008) Enantioselective synthesis of SNAP-7941: chiral dihydropyrimidone inhibitor of MCH1-R. J Org Chem 73:7651-7656. doi: 10.1021/jo801463j