Recent advances in chemistry of γ-lactams: Part II. Functionalization by C-C or C-heteroatom bond formation

Current Organic Chemistry

Volumn 18, Issue 12, 2014, Pages 1539-1585

  Martelli, Gianluca ^a   Monsignori, Antonella ^a   Orena, Mario ^a   Rinaldi, Samuele ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Enantioselectivity; Functionalization; Lactams; Stereoselectivity; Synthetic methods

Indexed keywords

AMIDES; CHEMICAL BONDS; SYNTHESIS (CHEMICAL);

BOND FORMATION; FUNCTIONALIZATIONS; HETEROATOM BONDS; LACTAM; MEDICINAL PRODUCTS; NATURAL PRODUCTS CHEMISTRY; NOVEL METHODOLOGY; PYRROLIDIN-2-ONES; SYNTHETIC METHODS; Γ-LACTAMS;

ENANTIOSELECTIVITY;

EID: 84906895763     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272819666140407213209     Document Type: Review

References (186)

1. Jiang, R.W.; Hon, P.M.; Xu, Y.T.; Chan, Y.M.; Xu, H.X.; Shaw, P.C.; But, P.P.H. Isolation and chemotaxonomic significance of tuberostemospironinetype alkaloids from Stemona tuberosa. Phytochemistry, 2006, 67, 52-57.
2. Zhou, C.X.; Zou, L.; Gan, L.S.; Cao, Y.L. Kleinhospitines A-D, new cycloartane triterpenoid alkaloids from Kleinhovia hospita. Org. Lett., 2013, 15, 2734-2737.
3. Aoki, S.-y.; Tsukude, T.; Miyazaki, Y.; Takao, K.-i.; Tadano, K.-i. Total synthesis of (-)-pramanicin. Heterocycles, 2006, 69, 49-54.
4. Kang, F.A.; Sui, Z. A diversity-oriented-synthesis protocol for scaffold discovery based on a general synthetic route to spirocycles. Tetrahedron Lett., 2011, 52, 4204-4206.
5. Enders, D.; Teschner, P.; Raabe, G.; Runsink, J. Asymmetric electrophilic substitutions at the α-position of γ-and δ-lactams. Eur. J. Org. Chem., 2001, 2001, 4463-4477.
6. Galeazzi, R.; Martelli, G.; Mobbili, G.; Orena, M.; Panagiotaki, M. A stereoselective approach to both 3,4-trans-disubstituted pyrrolidin-2-ones and pyrrolidines. A convenient synthesis of (3R,4R)-4-benzyl-3-pyrrolidinecarboxylic acid. Heterocycles, 2003, 60, 2485-2498.
7. Galeazzi, R.; Martelli, G.; Mobbili, G.; Orena, M.; Rinaldi, S. Synthesis of a conformationally restricted analog of pregabalin by stereoselective alkylation of a chiral pyrrolidin-2-one. Tetrahedron: Asymmetry, 2003, 14, 3353-3358.
8. Davies, S.G.; Garner, A.C.; Goddard, E.C.; Kruchinin, D.; Roberts, P.M.; Smith, A.D.; Rodriguez-Solla, H.; Thomson, J.E.; Toms, S.M. Asymmetric synthesis of 3,4-anti-and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition. Org. Biomol. Chem., 2007, 5, 1961-1969.
9. Craig, D.; Hyland, C.J.T.; Ward, S.E. Stereoselective γ-lactam synthesis via palladium-catalysed intramolecular allylation. Chem. Commun., 2005, (27), 3439-3441.
10. Crucianelli, E.; Galeazzi, R.; Martelli, G.; Orena, M.; Rinaldi, S.; Sabatino, P. A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones. Tetrahedron, 2010, 66, 400-405.
11. Galeazzi, R.; Martelli, G.; Orena, M.; Rinaldi, S. Stereoselective alkylation of chiral pyrrolidin-2-ones leading to novel conformationally restricted analogues of 3-methylaspartic acid: a computational investigation. Monatsh. Chem., 2012, 143, 1397-1403.
12. Yoon, C.H.; Flanigan, D.L.; Yoo, K.S.; Jung, K.W. Stereogenic evolution of clasto-lactacystin β-lactone from L-serine. Eur. J. Org. Chem., 2007, 2007, 37-39.
13. Martelli, G.; Orena, M.; Rinaldi, S., unpublished results.
14. Masschelein, K.G.R.; Stevens, C.V.; Dieltiens, N.; Claeys, D.D. Exploiting the regioselectivity of pyroglutamate alkylations for the synthesis of 6-azabicyclo[3.2.1]octanes and 4-azabicyclo[3.3.0]octanes. Tetrahedron, 2007, 63, 4712-4724.
15. Crucianelli, E.; Martelli, G.; Orena, M.; Rinaldi, S.; Sgolastra, F. New isosteres of (R)-2-methylhomoserine and (R)-2-methylaspartic acid by alkylation of a chiral imine leading stereoselectively to a quaternary stereogenic center. Tetrahedron: Asymmetry, 2009, 20, 1824-1827.
16. Raghavan, B.; Johnson, R.L. Short stereoselective synthesis of β-substituted γ-lactams. J. Org. Chem., 2006, 71, 2151-2154.
17. Agouridas, V.; Capet, F.; Couture, A.; Deniau, E.; Grandclaudon, P. A highly diastereoselective synthesis of isoindolinone-centered Meyers' tetracyclic lactams. Application to the asymmetric synthesis of 3-alkylisoindolinones. Tetrahedron: Asymmetry, 2011, 22, 1441-1447.
18. Zhang, Y.; Wang, S.Y.; Xu, X.P.; Jiang, R.; Ji, S.J. Asymmetric α-alkylation of aldehydes with 3-hydroxy-3-indolylox-indoles in aqueous media. Org. Biomol. Chem., 2013, 11, 1933-1937.
19. Zuo, J.; Liao, Y.H.; Zhang, X.M.; Yuan, W.C. Organocatalyzed enantioselective decarboxylative stereoablation reaction for the construction of 3,3-disubstituted oxindoles using β-ketoacids and 3-halooxindoles. J. Org. Chem., 2012, 77, 11325-11332.
20. Duan, Z.; Han, J.; Qian, P.; Zhang, Z.; Wang, Y.; Pan, Y. Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins. Org. Biomol. Chem., 2013, 11, 6456-6459.
21. Franckevičius, V.; Cuthbertson, J.D.; Pickworth, M.; Pugh, D.S.; Taylor, R.J.K. Asymmetric decarboxylative allylation of oxindoles. Org. Lett., 2011, 13, 4264-4267.
22. Shen, H.C.; Ding, F.X.; Colletti, S.L. α-Heteroarylation of esters, lactones, amides, and lactams by nucleophilic aromatic substitution. Org. Lett., 2006, 8, 1447-1450.
23. Moglioni, A.G.; Brousse, B.N.; Alvarez-Larena, A.; Moltrasio, G.Y.; Ortuño, R.M. Stereoselective synthesis of cyclobutyl GABA analogues and related compounds from (-)-(S)-verbenone. Tetrahedron: Asymmetry, 2002, 13, 451-454.
24. Kim, G.; Kim, J.H.; Lee, K.Y. New Palladium-catalyzed reaction pathway to the Erythrina skeleton. J. Org. Chem., 2006, 71, 2185-2187.
25. De la Fuente, M.C.; Dominguez, D. Synthesis of pyrrolo-and pyrido[1,2-a]xanthene [1,9-de]azepines: A study of the azepine ring construction. J. Org. Chem., 2007, 72, 8804-8810.
26. Awuah, E.; Capretta, A. Development of methods for the synthesis of libraries of substituted maleimides and α, β-unsaturated-γ-butyrolactams. J. Org. Chem., 2011, 76, 3122-3130.
27. Maryanoff, B.E.; Zhang, H.C.; Cohen, J.H.; Turchi, I.J.; Maryanoff, C.A. Cyclizations of N-acyliminium ions. Chem. Rev., 2004, 104, 1431-1628.
28. Yazici, A.; Pyne, S.G. Intermolecular addition reactions of N-acyliminium ions (Part I). Synthesis, 2009, 339-368.
29. Yazici, A.; Pyne, S.G. Intermolecular addition reactions of N-acyliminium ions (Part II). Synthesis, 2009, 513-541.
30. Padwa, A.; Rashatasakhon, P.; Rose, M. Triflic anhydride mediated cyclization of 5-hydroxy-substituted pyrrolidinones for the preparation of α-trifluoromethylsulfonamido furans. J. Org. Chem., 2003, 68, 5139-5146.
31. Kende, A.S.; Hernando, J.I.M.; Milbank, J.B.J. First total synthesis of (±)-Stemonamide and (±)-Isostemonamide. Org. Lett., 2001, 3, 2505-2508.
32. Kende, A.S.; Hernando J.I.M.; Milbank, J.B.J. Total synthesis of (±)-stemonamide and (±)-isostemonamide. Tetrahedron, 2002, 58, 61-74.
33. Alibés, R.; Bayón, P.; de March, P.; Figueredo, M.; Font, J.; García-García, E.; González-Gálvez D. An effective enantioselective approach to the Securinega alkaloids: total synthesis of (-)-Norsecurinine. Org. Lett., 2005, 7, 5107-5109.
34. González-Gálvez, D.; García-García, E.; Alibés, R.; Bayón, P.; de March, P.; Figueredo, M.; Font, J. Enantioselective approach to Securinega alkaloids. Total synthesis of Securinine and (-)-Norsecurinine. J. Org. Chem., 2009, 74, 6199-6211.
35. Katritzky, A.R.; Mehta, S.; He, H.Y. Syntheses of pyrrolo-and indoloisoquinolinones by intramolecular cyclizations of 1-(2-arylethyl)-5-benzotriazolylpyrrolidin-2-ones and 3-benzotriazolyl-2-(2-arylethyl)-1-isoindolinones. J. Org. Chem., 2001, 66, 148-152.
36. Katritzky, A.R.; He, H.Y.; Jiang, R. Convenient syntheses of dihydropyrrolo[2',1':3,4] pyrazino-and dihydropyrrolo[2',1':3,4][1,4] diazepino-[2,1-a]isoindolones. Tetrahedron Lett., 2002, 43, 2831-2833.
37. Cai, Q.; Liang, X.W.; Wang, S.G.; Zhang, J.W.; Zhang, X.; You, S.L. Ringclosing metathesis /isomerization/Pictet-Spengler cascade via Ruthenium/ chiral phosphoric acid sequential catalysis. Org. Lett., 2012, 14, 5022-5025.
38. Rueping, M.; Nachtsheim, B.J. Asymmetric Brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions. Synlett, 2010, (1), 119-122.
39. Bailey, P.D.; Morgan, K.M.; Smith, D.I.; Vernon, J.M. Spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile. Tetrahedron, 2003, 59, 3369-3378.
40. de Carné-Carnavalet, B.; Archambeau, A.; Meyer, C.; Cossy, J.; Folléas, B.; Brayer, J.L.; Demoute, J.P. Efficient synthesis of substituted 3-azabicyclo[3.1.0]hexan-2-ones from 2-iodocyclopropanecarboxamides using a Copper-free Sonogashira coupling. Chem. Eur. J., 2012, 18, 16716-16727.
41. Padwa, A.; Lee, H.I.; Rashatasakhon, P.; Rose, M. Electrophilic-induced cyclization reaction of hexahydroindolinone derivatives and its application toward the synthesis of (±)-Erysotramidine. J. Org. Chem., 2004, 69, 8209-8218.
42. Bahajaj, A.A.; Vernon, J.M., Wilson, G.D. Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 2: NAcyliminium ion cyclisations with an internal alkene nucleophile. Tetrahedron, 2004, 60, 1247-1253.
43. Bahajaj, A.A.; Vernon, J.M.; Wilson, G.D. Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: NAcyliminium ion cyclisations with an internal arene nucleophile. Tetrahedron, 2004, 60, 1235-1246.
44. Yoda, H.; Inoue, K.I.; Ujihara, Y.; Mase, N.; Takabe, K. Lewis acidpromoted tandem desulfurization and hydroxylation of γ-phenylthiosubstituted lactams: novel synthetic strategy of isoindolobenzazepine alkaloid, chilenine. Tetrahedron Lett., 2003, 44, 9057-9060.
45. Suzuki, T.; Takabe, K.; Yoda, H. Novel chemoselective desulfurization of γ-phenylthio-substituted aromatic lactams: Application to the synthesis of isoindolobenzazepine alkaloid, lennoxamine. Synlett, 2006, (20), 3407-3410.
46. Ye, Z.B.; Chen, J.; Meng, W.H.; Huang P.Q. N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: Asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B. Tetrahedron: Asymmetry, 2010, 21, 895-902.
47. Jiang, L.J.; Teng, B.; Zheng, J.F.; Ye, J.L.; Huang, P.Q. Bis-Lewis acidscatalyzed highly diastereoselective one-pot reductive dehydroxylation of chiral N, O-acetals. Tetrahedron, 2010, 66, 172-175.
48. Pin, F.; Comesse, S.; Garrigues, B.; Marchalín, S.; Daïch, A. Intermolecular and intramolecular α-amidoalkylation reactions using bismuth triflate as the catalyst. J. Org. Chem., 2007, 72, 1181-1191.
49. Pin, F.; Comesse, S.; Daïch, A. Association of intramolecular furan Diels-Alder reaction and N-acyliminium alkylation for the synthesis of pentacyclic precursor of aromathecins. Synlett, 2009, 3214-3218.
50. Morgan, I.R.; Yazici, A.; Pyne, S.G. Diastereoselective borono-Mannich reactions on cyclic N-acyliminium ions. Tetrahedron, 2008, 64, 1409-1419.
51. Vieira, A.S.; Ferreira, F.P.; Fiorante, P.F.; Guadagnin, R.C.; Stefani, H.A. Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic Nacyliminium ions: stereoselective synthesis of functionalized N-heterocycles. Tetrahedron, 2008, 64, 3306-3314.
52. Peterson, E.A.; Jacobsen, E.N. Enantioselective, thiourea catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ions. Angew. Chem. Int. Ed., 2009, 48, 6328-6331.
53. Xie, Y.; Zhao, Y.; Qian, B.; Yang, L.; Xia, C.; Huang, H. Enantioselective N-H functionalization of indoles with α, β-unsaturated γ-lactams catalyzed by chiral Brønsted acids. Angew. Chem. Int. Ed., 2011, 50, 5682-5686.
54. Zhou, J.Q.; Sheng, W.J.; Jia, J.H.; Ye, Q.; Gao, J.R.; Jia, Y.X. Chiral phosphoric acid catalyzed asymmetric hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones. Tetrahedron Lett., 2013, 54, 3082-3084.
55. Raheem, I.T.; Thiara, P.S.; Peterson, E.A.; Jacobsen, E.N. Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding. J. Am. Chem. Soc., 2007, 129, 13404-13405.
56. Muratore, M.E.; Holloway, C.A.; Pilling, A.W.; Storer, R.I.; Trevitt, G.; Dixon, D.J. Enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascades. J. Am. Chem. Soc., 2009, 131, 10796-10797.
57. Yang, T.; Campbell, L.; Dixon, D.J. A Au(I)-catalyzed N-acyl iminium ion cyclization cascade. J. Am. Chem. Soc., 2007, 129, 12070-12071.
58. Hu, K.Z.; Ma, J.; Qiu, S.; Zheng, X.; Huang, P.Q. SmI2-Mediated intermolecular coupling of γ-lactam N-α-radicals with activated alkenes: asymmetric synthesis of 11-hydroxylated analogues of the lead compounds CP-734432 and PF-04475270. J. Org. Chem., 2013, 78, 1790-1801.
59. Wang, X.G.; Wang, A.E.; Hao, Y.; Ruan, Y.P.; Huang, P.Q. Modular enantioselective synthesis of 8-Aza-prostaglandin E1. J. Org. Chem., 2013, 78, 9488-9493.
60. Sinha, N.; Jain, S.; Anand, N. A novel and unusual method for C-N bond formation in 1-substituted-pyrrolidin-2-ones. Tetrahedron Lett., 2005, 46, 153-156.
61. Gallagher, T.; Derrick, I.; Durkin, P.M.; Haseler, C.A.; Hirschhauser, C.; Magrone, P. Intramolecular 1,6-addition to 2-pyridones. Mechanism and synthetic scope. J. Org. Chem., 2010, 75, 3766-3774.
62. Bogle, K.M.; Hirst, D.J.; Dixon, D.J. Total synthesis of (±)-Powelline and (±)-Buphanidrine. Org. Lett., 2010, 12, 1252-1254.
63. Brana, M.F.; Garranzo, M.; de Pascual-Teresa, B.; Perez-Castells, J.; Torres, M.R. Chemoselective Michael reactions on pyroglutamates. Expeditious synthesis of spiro-bis-γ-lactams as β-turn peptidomimetics. Tetrahedron, 2002, 58, 4825-4836.
64. Rege, P.D.; Johnson, F. Application of vicarious nucleophilic substitution to the total synthesis of dl-Physostigmine. J. Org. Chem., 2003, 68, 6133-6139.
65. Sartori, A.; Curti, C.; Battistini, L.; Burreddu, P.; Rassu, G.; Pelosi, G.; Casiraghi, G.; Zanardi, F. Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors. Tetrahedron, 2008, 64, 11697-11705.
66. Shepherd, N.E.; Tanabe, H.; Xu, Y.; Matsunaga, S.; Shibasaki, M. Direct catalytic asymmetric vinylogous Mannich-type and Michael reactions of an α, β-unsaturated γ-butyrolactam under dinuclear Nickel catalysis. J. Am. Chem. Soc., 2010, 132, 3666-3667.
67. Feng, X.; Cui, H.L.; Xu, S.; Wu, L.; Chen, Y.C. Organocatalytic direct vinylogous Michael addition of α, β-unsaturated γ-butyrolactam to α, β-unsaturated aldehydes and an illustration to scaffold diversity synthesis. Chem. Eur. J., 2010, 16, 10309-10312.
68. Huang, H.; Jin, Z.; Zhu, K.; Liang, X.; Ye, J. Highly diastereo-and enantioselective synthesis of 5-substituted 3-pyrrolidin-2-ones: vinylogous Michael addition under multifunctional catalysis. Angew. Chem. Int. Ed., 2011, 50, 3232-3235.
69. Zhang, Y.; Shao, Y.L.; Xu, H.S.; Wang, W. Organocatalytic direct asymmetric vinylogous Michael reaction of an α, β-unsaturated γ-butyrolactam with enones. J. Org. Chem., 2011, 76, 1472-1474.
70. Marcos, I.; Redero, E.; Bermejo, F. Synthetic studies towards (+)-Dihydroampullicin. Michael addition of N-Boc-2-(tert-butyldimethylsiloxy)-3-methylpyrrole to α-methylene lactones. Tetrahedron Lett., 2000, 41, 8451-8455.
71. Arroyo, Y.; de Paz, M.; Rodríguez, J.F.; Sanz-Tejedor, M.A.; García Ruano, J.L. Diastereoselective Michael additions of N-Boc-2-(tert-butyldimethylsiloxy) pyrrole to 2-(arylsulfinyl)-1,4-benzoquinones. J. Org. Chem., 2002, 67, 5638-5643.
72. Kamimura, A.; Nagata, Y.; Kadowaki, A.; Uchida, K.; Uno, H. Stereoselective conjugate addition of lactams to nitroalkenes and formal total synthesis of indolizidine 167B. Tetrahedron, 2007, 63, 11856-11861.
73. Belliotti, T.R.; Capiris, T.; Ekhato, I.V.; Kinsora, J.J.; Field, M.J.; Heffner, T.G.; Meltzer, L.T.; Schwarz, J.B.; Taylor, C.P.; Thorpe, A.J.; Vartanian, M.G.; Wise, L.D.; Zhi-Su, T.; Weber, M.L.; Wustrow, D.J. Structure-activity relationships of Pregabalin and analogues that target the α2-δ protein. J. Med. Chem., 2005, 48, 2294-2307.
74. Spiess, S.; Berthold, C.; Weihofen, R.; Helmchen, G. Synthesis of α, β-unsaturated γ-lactams via asymmetric iridium-catalysed allylic substitution. Org. Biomol. Chem., 2007, 5, 2357-2360.
75. Hara, S.; Makino, K.; Hamada, Y. Stereoselective synthesis of protected (2S,3S)-N-methyl-5-hydroxyisoleucine, a component of halipeptins. Tetrahedron, 2004, 60, 8031-8035.
76. Bentz, E.L.; Goswami, R.; Moloney, M.G.; Westaway, S.M. Stereoselective synthesis of conformationally constrained ω-amino acids analogues from pyroglutamic acid. Org. Biomol. Chem., 2005, 3, 2872-2882.
77. DeGoey, D.A.; Chen, H.J.; Flosi, W.J.; Grampovnik, D.J.; Yeung, C.M.; Klein, L.L.; Kempf, D.J. Enantioselective synthesis of antiinfluenza compound A-315675. J. Org. Chem., 2002, 67, 5445-5453.
78. Barnes, D.M.; Bhagavatula, L.; DeMattei, J.; Gupta, A.; Hill, D.R.; Manna, S.; McLaughlin, M.A.; Nichols, P.; Premchandran, R.; Rasmussen, M.W.; Tian, Z.; Wittenberger, S.J. A highly diastereoselective vinylogous Mannich condensation and 1,4-conjugate addition of (Z)-propenyl cuprate in the synthesis of an influenza neuraminidase inhibitor. Tetrahedron: Asymmetry, 2003, 14, 3541-3551.
79. Shao, C.; Yu, H.J.; Wu, N.Y.; Tian, P.; Wang, R.; Feng, C.G.; Lin, G.Q. Asymmetric synthesis of β-substituted γ-lactams via Rhodium/dienecatalyzed 1,4-additions: Application to the synthesis of (R)-Baclofen and (R)-Rolipram. Org. Lett., 2011, 13, 788-791.
80. Kuuloja, N.; Vaismaa, M.; Franzén, R. Rh-IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone. Tetrahedron, 2012, 68, 2313-2318.
81. Camarero, C.; Gonzalez-Temprano, I.; Gomez-SanJuan, A.; Arrasate, S.; Lete, E.; Sotomayor, N. Stereocontrolled conjugate additions to dihydroindolizinone systems. Synthesis of enantiopure polysubstituted tetrahydropyrrolo[2,1-a]isoquinolones. Tetrahedron, 2009, 65, 5787-5798.
82. Camarero, C.; Arrasate, S.; Sotomayor, N.; Lete, E. A DITOX derived α-sulfinylcarbanion as nucleophile in conjugate addition reactions to pyrrolo[2,1a]isoquinolones. Arkivoc, 2010, 45-55.
83. Nam, N.H.; Kim, Y.; You, Y.J.; Hong, D.H.; Kim, H.M.; Ahn, B.Z. Synthesis and citotoxicity of some rigid derivatives of methyl 2,5-dihydroxycinnamate. Arch. Pharm. Res., 2002, 25, 590-599.
84. Sikriwal, D.; Kant, R.; Maulik, P.R.; Dikshit, D.K. A short formal synthesis of three epimers of penmacric acid. Tetrahedron, 2010, 66, 6167-6173.
85. Zanardi, F.; Curti, C.; Sartori, A.; Rassu, G.; Roggio, A.; Battistini, L.; Burreddu, P.; Pinna, L.; Pelosi, G.; Casiraghi, G. Further uses of pyrrolebased dienoxysilane synthons: A full aldol approach to azabicyclo[x.2.1]alkane systems. Eur. J. Org. Chem., 2008, 2008, 2273-2287.
86. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. The vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver. Chem. Rev., 2000, 100, 1929-1972.
87. Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. The vinylogous aldol and related addition reactions: Ten years of progress. Chem. Rev., 2011, 111, 3076-3154.
88. Das Sarma, K.; Zhang, J.; Curran, T.T. Novel synthons from mucochloric acid: the first use of α, β-dichloro-γ-butenolides and γ-butyrolactams for direct vinylogous aldol addition. J. Org. Chem., 2007, 72, 3311-3318.
89. Miyazaki, H.; Ogiku, T.; Sai, H.; Moritani, Y.; Ohtani, A.; Ohmizu, H. Synthesis and evaluation of pyrrolin-2-one compounds, a series of plasminogen activator inhibitor-1 inhibitors. Chem. Pharm. Bull., 2009, 57, 979-985.
90. Li, W.R.; Lin, S.T.; Hsu, N.M.; Chern, M.S. Efficient total synthesis of Pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor. J. Org. Chem., 2002, 67, 4702-4706.
91. Lautens, M.; Han, W.; Liu, J.H.C. MgI2-Mediated ring expansions of secondary methylenecyclopropyl amides. J. Am. Chem. Soc., 2003, 125, 4028-4029.
92. Planas, L.; Pérard-Viret, J.; Royer, J. Stereoselective synthesis of (-)-Cephalotaxine and C-7 alkylated analogues. J. Org. Chem., 2004, 69, 3087-3092.
93. Baussanne, I.; Dudot, B.; Pérard-Viret, J.; Planas, L.; Royer, J. New developments in the asymmetric synthesis of heterocyclic natural products. Arkivoc, 2006, 57-66.
94. Curti, C.; Sartori, A.; Battistini, L.; Rassu, G.; Burreddu, P.; Zanardi, F.; Casiraghi, G. Vicarious silylative Mukaiyama aldol reaction: A vinylogous extension. J. Org. Chem., 2008, 73, 5446-5451.
95. Curti, C.; Battistini, L.; Zanardi, F.; Rassu, G.; Zambrano, V.; Pinna, L.; Casiraghi, G. Uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reactions on aqueous media: pyrrole vs furan 2-silyloxy dienes. J. Org. Chem., 2010, 75, 8681-8684.
96. Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. The utility of furan-, pyrrole-, and thiophenebased 2-silyloxy dienes as demonstrated by modular synthesis of annonaceous acetogenin core units and their pyrrolidine and thiolane analogues. J. Org. Chem., 2000, 65, 2048-2064.
97. Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Zanardi, F.; Battistini, L.; Gaetani, E.; Curti, C.; Casiraghi, G. Variable strategy toward carbasugars and relatives. 5. Focus on preparation of chiral nonracemic medium-sized carbocycles. J. Org. Chem., 2003, 68, 5881-5885.
98. Battistini, L.; Curti, C.; Zanardi, F.; Rassu, G.; Auzzas, L.; Casiraghi, G. Enantioselective total synthesis of (1R,3S,4R,5R)-1-amino-4,5-dihydroxycyclopentane-1,3-dicarboxylic acid. A full-aldol access to carbaketose derivatives. J. Org. Chem., 2004, 69, 2611-2613.
99. Rassu, G.; Zambrano, V.; Tanca, R.; Sartori, A.; Battistini, L.; Zanardi, F.; Curti, C.; Casiraghi, G. 3-Alkenyl-2-silyloxyindoles: An enabling, yet understated progeny of vinylogous carbon nucleophiles. Eur. J. Org. Chem., 2012, 2012, 466-470.
100. Curti, C.; Sartori, A.; Battistini, L.; Rassu, G.; Zanardi, F.; Casiraghi, G. Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of α, β-unsaturated γ-butyrolactam synthons. Tetrahedron Lett., 2009, 50, 3428-3431.
101. Frings, M.; Atodiresei, I.; Wang, Y.; Runsink, J.; Raabe, G.; Bolm, C. C1-Symmetric aminosulfoximines in Copper-catalyzed asymmetric vinylogous Mukaiyama aldol reactions. Chem. Eur. J., 2010, 16, 4577-4587.
102. Dudot, B.; Chiaroni A.; Royer J. Yb(OTf)3-catalyzed Mannich-type reaction of a chiral non-racemic silyloxypyrrole. Tetrahedron Lett., 2000, 41, 6355-6359.
103. Barnes, D.M.; McLaughlin, M.A.; Oie, T.; Rasmussen, M.W.; Stewart, K.D.; Wittenberger, S.J. Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction. Org. Lett., 2002, 4, 1427-1430.
104. Curti, C.; Battistini, L.; Ranieri, B.; Pelosi, G.; Rassu, G.; Casiraghi, G.; Zanardi, F. anti-Selective, catalytic asymmetric vinylogous Mukaiyama-Mannich reactions of pyrrole-based silyldienolates with N-aryl aldimines. J. Org. Chem., 2011, 76, 2248-2252.
105. Ranieri, B.; Curti, C.; Battistini, L.; Sartori, A.; Pinna, L.; Casiraghi, G.; Zanardi, F. Diastereo-and enantioselective catalytic vinylogous Mukaiyama-Mannich reactions of pyrrole-based silyl dienolates with alkyl-substituted aldehydes. J. Org. Chem., 2011, 76, 10291-10298.
106. Camps, P.; Gómez, T.; Muñoz-Torrero, D.; Rull, J.; Sánchez, L.; Boschi, F.; Comes-Franchini, M.; Ricci, A.; Calvet, T.; Font-Bardia, M.; De Clercq, E.; Naesens L. Synthesis and absolute configuration of novel N, Opsiconucleosides using (R)-N-phenylpantolactam as a resolution agent. J. Org. Chem., 2008, 73, 6657-6665.
107. Paraskar, A.S.; Sudalai, A. Co-catalyzed reductive cyclization of azido and cyano substituted α, β-unsaturated esters with NaBH4: Enantioselective synthesis of (R)-baclofen and (R)-rolipram. Tetrahedron, 2006, 62, 4907-4916.
108. Blanchet, J.; Pouliquen, M.; Lasne, M.C.; Rouden, J. A rapid and convenient synthesis of β-proline. Tetrahedron Lett., 2007, 48, 5727-5730.
109. Perseghini, M.; Massaccesi, M.; Liu, Y.; Togni, A. Structural and stereochemical aspects of the enantioselective halogenation of 1,3-dicarbonyl compounds catalyzed by Ti(TADDOLato) complexes. Tetrahedron, 2006, 62, 7180-7190.
110. Suzuki, T.; Goto, T.; Hamashima, Y.; Sodeoka, M. Enantioselective fluorination of tert-butoxycarbonyl lactones and lactams catalyzed by chiral Pd(II)-bisphosphine complexes. J. Org. Chem., 2007, 72, 246-250.
111. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. Catalytic enantioselective fluorination of oxindoles. J. Am. Chem. Soc., 2005, 127, 10164-10165.
112. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles. Angew. Chem. Int. Ed., 2008, 47, 4157-4161.
113. Shibata, N.; Kohno, J.; Takai, K.; Ishimaru, T.; Nakamura, S.; Toru, T.; Kanemasa, S. Highly enantioselective catalytic fluorination and chlorination reactions of carbonyl compounds capable of two-point binding. Angew. Chem. Int. Ed., 2005, 44, 4204-4207.
114. Deng, Q.H.; Wadepohl, H.; Gade, L.H. The synthesis of a new class of chiral pincer ligands and their applications in enantioselective catalytic fluorinations and the Nozaki-Hiyama-Kishi reaction. Chem. Eur. J., 2011, 17, 14922-14928.
115. Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M. Enantioselective fluorination mediated by Cinchona alkaloid derivatives/Selectfluor combinations: Reaction scope and structural information for N-fluorocinchona alkaloids. J. Am. Chem. Soc., 2001, 123, 7001-7009.
116. Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K.L. Enantioselective fluorination mediated by N-fluoroammonium salts of Cinchona alkaloids: first enantioselective synthesis of BMS-204352 (MaxiPost). J. Org. Chem., 2003, 68, 2494-2497.
117. Li, J.; Cai, Y.; Chen, W.; Liu, X.; Lin, L.; Feng, X. Highly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost). J. Org. Chem., 2012, 77, 9148-9155.
118. Loreto, M.A.; Migliorini, A.; Tardella, P.A.; Gambacorta A. Novel spiroheterocycles by aziridination of α-methylene-γ-and-δ-lactams. Eur. J. Org. Chem., 2007, 2007, 2365-2371.
119. Shionozaki, N.; Iwamura, N.; Tanaka, R.; Makino, K.; Uchiro, H. Total synthesis of Diaporthichalasin by using the intramolecular Diels-Alder reaction of an α, β-unsaturated γ-hydroxylactam in aqueous media. Chem. Asian J., 2013, 8, 1243-1252.
120. Jakubec, P.; Cockfield, D.M.; Dixon, D.J. Total synthesis of (-)-Nakadomarin A. J. Am. Chem. Soc., 2009, 131, 16632-16633.
121. Resek, J.E. Intramolecular ene reaction of a chiral bicyclic lactam. J. Org. Chem., 2008, 73, 9792-9794.
122. Albrecht, D.; Basler, B.; Bach, T. Preparation and intramolecular [2+2]-photocycloaddition of 1,5-dihydropyrrol-2-ones and 5,6-dihydro-1H-pyridin-2-ones with C-, N-, and O-linked alkenyl side chains at the 4-position. J. Org. Chem., 2008, 73, 2345-2356.
123. Padwa, A.; Jacquez, M.N.; Schmidt, A. Intramolecular photocycloaddition of cyclic thioimides as a method for heterocyclic synthesis. Org. Lett., 2001, 3, 1781-1783.
124. Padwa, A.; Jacquez, M.N.; Schmidt, A. An approach toward azacycles using photochemical and radical cyclizations of N-alkenyl substituted 5-thioxopyrrolidin-2-ones. J. Org. Chem., 2004, 69, 33-45.
125. Kang, S.W.; Kim, Y.H.; Kim, H.J.; Lee, J.H.; Kim, S.H. A convenient synthesis of polycyclic γ-lactams via Pauson-Khand reaction. Bull. Korean Chem. Soc., 2009, 30, 691-694.
126. Wee, A.G.H.; Fan, G.J.; Bayirinoba, H.M. Nonracemic bicyclic lactam lactones via regio-and cis-diastereocontrolled C-H insertion. Asymmetric synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol. J. Org. Chem., 2009, 74, 8261-8271.
127. Aszodi, J.; Rowlands, D.A.; Mauvais, P.; Collette, P.; Bonnefoy, A.; Lampilas, M. Design and synthesis of bridged γ-lactams as analogues of γ-lactam antibiotics. Bioorg. Med. Chem. Lett., 2004, 14, 2489-2492.
128. Reddy, B.V.S.; Karthik, G.; Rajasekaran, T.; Antony, A.; Sridhar, B. Rh2(OAc)4 catalyzed substrate selective [4+2]/[2+2] cycloaddition of acylketenes: A highly chemo-and regioselective synthesis of spiro(oxindolyl) oxazinones and γ-lactams. Tetrahedron Lett., 2012, 53, 2396-2401.
129. DeAngelis, A.; Dmitrenko, O.; Fox, J.M. Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration. J. Am. Chem. Soc., 2012, 134, 11035-11043.
130. Li, M.; Dixon, D.J. Stereoselective spirolactam synthesis via palladium catalyzed arylative allene carbocyclization cascades. Org. Lett., 2010, 12, 3784-3787.
131. Yong, S.R.; Williams, M.C.; Pyne, S.G.; Ung, A.T.; Skelton, B.W.; White, A.H.; Turner, P. Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphinecatalyzed [3+2]-cycloadditions. Tetrahedron, 2005, 61, 8120-8129.
132. Day, J.; Uroos, M.; Castledine, R.A.; Lewis, W.; McKeever-Abbas, B.; Dowden, J. Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides. Org. Biomol. Chem., 2013, 11, 6502-6509.
133. Sun, J.; Xie, Y.J.; Yan, C.G. Construction of dispirocyclopentanebisoxindoles via self-domino Michael-aldol reactions of 3-phenacylideneoxindoles. J. Org. Chem., 2013, 78, 8354-8365.
134. Jao, E.; Bogen, S.; Saksena, A.K.; Girijavallabhan, V. [3+2] Cycloaddition of trimethylenemethane (TMM) to α, β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates. Tetrahedron Lett., 2003, 44, 5033-5035.
135. André, V.; Vidal, A.; Ollivier, J.; Robin, S.; Aitken, D.J. Rapid access to ciscyclobutane γ-amino acids in enantiomerically pure form. Tetrahedron Lett., 2011, 52, 1253-1255.
136. André, V.; Gras, M.; Awada, H.; Guillot, R.; Robin, S.; Aitken, D.J. A unified synthesis of all stereoisomers of 2-(aminomethyl)cyclobutane-1-carboxylic acid. Tetrahedron, 2013, 69, 3571-3576.
137. Karstens, W.F.J.; Stol, M.; Rutjes, F.P.J.T.; Kooijman, H.; Spek, A.L.; Hiemstra, H. Palladium catalyzed cyclization reactions of acetylenic lactams. J. Organomet. Chem., 2001, 624, 244-258.
138. Alonso, F.; Beletskaya, I.P.; Yus, M. Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes. Chem. Rev., 2004, 104, 3079-3159.
139. Zeni, G.; Larock, R.C. Synthesis of heterocycles via Palladium-catalyzed oxidative addition. Chem. Rev., 2006, 106, 4644-4680.
140. Bencivenni, G.; Wu, L.Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.P.; Bartoli, G.; Melchiorre, P. Targeting structural and stereochemical complexity by organocascade catalysis: Construction of spirocyclic oxindoles having multiple stereocenters. Angew. Chem. Int. Ed., 2009, 48, 7200-7203.
141. Sundar, J.K.; Rajesh, S.M.; Sivamani, J.; Perumal, S.; Natarajan, S. Synthesis and crystal structures of 5'-phenylspiro[indoline-3,2'-pyrrolidin]-2-one derivatives. Chem. Centr. J., 2011, 5, 45.
142. Byk, G.; Kabha, E. A solid-supported stereoselective multicomponent reaction: One-pot generation of three asymmetric carbons. Synlett, 2006, (5), 747-748.
143. Lo, M.M.C.; Neumann, C.S.; Nagayama, S.; Perlstein, E.O.; Schreiber, S.L. A library of spirooxindoles based on a stereoselective three-component coupling reaction. J. Am. Chem. Soc., 2004, 126, 16077-16086.
144. Albrecht, A.; Albrecht, Ł.; Janecki, T. Recent advances in the synthesis of α-alkylidene-substituted δ-lactones, γ-lactams and δ-lactams. Eur. J. Org. Chem., 2011, 2011, 2747-2766.
145. Krawczyk, H.; Albrecht, Ł.; Wojciechowski, J.; Wolf, M.W. Spontaneous Nef reaction of 3-aryl-2-(diethoxyphosphoryl)-4-nitroalkanoic acids. Tetrahedron, 2006, 62, 9135-9145.
146. Krawczyk, H.; Albrecht, Ł.; Wojciechowski, J.; Wolf, W.M.; Krajewska, U.; Róalski, M. A convenient synthesis and cytotoxic evaluation of Nunsubstituted α-methylene-γ-lactams. Tetrahedron, 2008, 64, 6307-6314.
147. Albrecht, A.; Koszuk, J.F.; Modranka, J.; Róalski, M.; Krajewska, U.; Janecka, A.; Studzian, K.; Janecki, T. Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams. Bioorg. Med. Chem., 2008, 16, 4872-4882.
148. Yajima, T.; Hamano, M.; Nagano, H. Highly cis-and trans-selective alkyl radical addition to α-methylene-γ-phenyl-γ-butyrolactams. Tetrahedron Lett., 2009, 50, 1301-1302.
149. Elford, T.G.; Ulaczyk-Lesanko, A.; De Pascale, G.; Wright, G.D.; Hall. D.G. Diversity-oriented synthesis and preliminary biological screening of highly substituted five-membered lactones and lactams originating from an allyboration of aldehydes and imines. J. Comb. Chem., 2009, 11, 155-168.
150. Zhou, X.; Liu, W.J.; Ye, J.L.; Huang, P.Q. Complementary stereocontrolled approaches to 2-pyrrolidinones bearing a vicinal amino diol subunit with three continuous chiral centers: A formal asymmetric synthesis of (-)-Detoxinine. J. Org. Chem., 2007, 72, 8904-8909.
151. Kralj, D.; Grošelj, U.; Meden, A.; Dahmann, G.; Stanovnik, B.; Svete, J. A simple synthesis of 4-(2-aminoethyl)-5-hydroxy-1H-pyrazoles. Tetrahedron, 2007, 63, 11213-11222.
152. Motherwell, W.B.; Begis, G.; Cladingboel, D.E.; Jerome, L.; Sheppard, T.D. Observations on the direct amidocyclopropanation of alkenes using organozinc carbenoids. Tetrahedron, 2007, 63, 6462-6476.
153. Pinheiro, S.; da Silva Júnior, R.C.; de Souza, A.S.; de M. Carneiro, J.W.; Muri, E.M.F.; Antunes, O.A.C. A general approach for the synthesis of 5-substituted-4-amino-pyrrolidin-2-ones and 5-substituted-4-amino-3-pyrrolin-2-ones. Tetrahedron Lett., 2009, 50, 2402-2404.
154. Haldar, P.; Ray, J.K. NaBH4-InCl3-mediated one-pot chemo and stereoselective decarboxylative reduction of α-aza gem-dicarboxylic esters to monoalcohols. Org. Lett., 2005, 7, 4341-4343.
155. Liu, Y.L.; Wang, B.L.; Cao, J.J.; Chen, L.; Zhang, Y.X.; Wang, C.; Zhou, J. Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via Morita-Baylis-Hillman reaction. J. Am. Chem. Soc., 2010, 132, 15176-15178.
156. Hu, F.L.; Wei, Y.; Shi, M.; Pindi, S.; Li, G. Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers. Org. Biomol. Chem., 2013, 11, 1921-1924.
157. Zhang, J.; Liu, X.; Ma, X.; Wang, R. Direct asymmetric aldol additionisomerization of α, β-unsaturated γ-butyrolactam with aryl α-ketoesters: Synthesis of MBH-type products. Chem. Commun., 2013, 49, 3300-3302.
158. Chandanshive, J.Z.; González, P.B.; Tiznado, W.; Bonini, B.F.; Caballero, J.; Femoni, C.; Comes-Franchini, M. 1,3-Dipolar cycloaddition of nitrile imines with α, β-unsaturated lactones, thiolactones and lactams: synthesis of ringfused pyrazoles. Tetrahedron, 2012, 68, 3319-3328.
159. Liu, Y.L.; Zhou, J. Organocatalytic asymmetric cyanation of isatin derived N-Boc ketoimines. Chem. Commun., 2013, 49, 4421-4423.
160. Galeazzi, R.; Martelli, G.; Marcucci, E.; Mobbili, G.; Natali, D.; Orena, M.; Rinaldi, S. A new conformationally restricted mimetic of dipeptide EG-Synthesis of an analog of FEG. Eur. J. Org. Chem., 2007, 2007, 4402-4407.
161. Camps, P.; Muñoz-Torrero, D.; Rull, J.; Font-Bardia, M.; Solans, X. Enantiodivergent synthesis of 3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one and derivatives: amino analogues of pantolactone. Tetrahedron: Asymmetry, 2007, 18, 2947-2958.
162. Camps, P.; Muñoz-Torrero, D.; Rull, J.; Antonio Mayoral, J.; Calvet, T.; Font-Bardia, M. Straightforward preparation of enantiopure 3-amino-4,4-dimethylpyrrolidin-2-one and its derivatives. Tetrahedron: Asymmetry, 2010, 21, 2124-2135.
163. Iley, J.; Tolando, R.; Constantino, L. Chemical and microsomal oxidation of tertiary amides: regio-and stereoselective aspects. J. Chem. Soc., Perkin Trans. 2, 2001, (8), 1299-1305.
164. Clark, R.W.; Maxwell Deaton, T.; Zhang, Y.; Moore, M.I.; Wiskur, S.L. Silylation-based kinetic resolution of α-hydroxy lactones and lactams. Org. Lett., 2013, 15, 6132-6135.
165. Felluga, F.; Gombac, V.; Pitacco, G.; Valentin, E. Biotransformations in the synthesis of 2-pyrrolidinones and 2-pyrrolinones. Targets Heterocycl. Syst., 2005, 9, 158-185.
166. Forró, E.; Fülöp, F. Enzymatic method for the synthesis of blockbuster drug intermediates-Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers. Eur. J. Org. Chem., 2008, 2008, 5263-5268.
167. Littlechild, J.A.; Guy, J.; Connelly, S.; Mallett, L.; Waddell, S.; Rye, C.A.; Line K.; Isupov, M. Natural methods of protein stabilization: thermostable biocatalysts. Biochem. Soc. Trans., 2007, 35, 1558-1563.
168. Toogood, H.; Brown, R.C.; Line, K.; Keene, P.; Taylor, S.; McCague, R.; Littlechild, J. The use of a thermostable signature amidase in the resolution of the bicyclic synthon (rac)-γ-lactam. Tetrahedron, 2004, 60, 711-716.
169. Singh, R.; Vince, R. 2-Azabicyclo[2.2.1]hept-5-en-3-one: chemical profile of a versatile synthetic building block and its impact on the development of therapeutics. Chem. Rev., 2012, 112, 4642-4686.
170. Torres, L.L.; Schließmann, A.; Schmidt, M.; Silva-Martin, N.; Hermoso, J.A.; Berenguer, J.; Bornscheuer, U.T.; Hidalgo, A. Promiscuous enantioselective (-)-γ-lactamase activity in the Pseudomonas fluorescens esterase I. Org. Biomol. Chem., 2012, 10, 3388-3392.
171. Qin, X.; Wang, J.; Zheng, G. Enantioselective resolution of γ-lactam by a whole cell of Microbacterium hydrocarbonoxydans (L29-9) immobilized in polymer of PVA-alginate-boric acid. Appl. Biochem. Biotechnol., 2010, 162, 2345-2354.
172. Bertoli, A.; Fanfoni, L.; Felluga, F.; Pitacco, G.; Valentin, E. Chemoenzymatic synthesis of optically active α-methylene-γ-carboxy-γ-lactams and γ-lactones. Tetrahedron: Asymmetry, 2009, 20, 2305-2310.
173. Felluga, F.; Ghelfi, F.; Pitacco, G.; Roncaglia, F.; Valentin, E.; Venneri, C.D. Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom. Tetrahedron: Asymmetry, 2010, 21, 2183-2191.
174. Chang, D.; Witholt, B.; Li, Z. Preparation of (S)-N-substituted 4-hydroxypyrrolidin-2-ones by regio and stereoselective hydroxylation with Sphingomonas sp. HXN-200. Org. Lett., 2000, 2, 3949-3952.
175. Pinheiro, L.; Buisson, D.; Cortial, S.; Delaforge, M.; Ouazzani, J. Microbial decyanation of 1-benzylpyrrolidine-2,5-dicarbonitrile. Mechanistic investigations. J. Mol. Cat. B: Enzymatic, 2011, 68, 211-215.
176. Seebach, D.; Matthews, J.L.-Peptides: A surprise at every turn. Chem. Commun., 1997, (21), 2015-2022.
177. Gellman, S.H. Foldamers: A manifesto. Acc. Chem. Res., 1998, 31, 173-180.
178. Venkatraman, J.; Shankaramma, S.C.; Balaram, P. Design of folded peptides. Chem. Rev., 2001, 101, 3131-3152.
179. Cheng, R.P.; Gellman, S.H.; DeGrado, W.F.-Peptides: From structure to function. Chem. Rev., 2001, 101, 3219-3232.
180. Hill, D.J.; Mio, M.J.; Prince, R.B.; Hughes, T.S.; Moore, J.S. A field guide to foldamers. Chem. Rev., 2001, 101, 3893-4011.
181. Seebach, D.; Hook, D.F.; Glättli A. Helices and other secondary structures of β-and γ-peptides. Biopolymers (Pept. Sci.), 2006, 84, 23-37.
182. Fülöp, F.; Martinek, T.A.; Tóth, G.K. Application of alicyclic-amino acids in peptide chemistry. Chem. Soc. Rev., 2006, 35, 323-334.
183. Horne, W.S.; Gellman, S.H. Foldamers with heterogeneous backbones. Acc. Chem. Res., 2008, 41, 1399-1408.
184. Martinek, T.A.; Fülöp, F. Peptidic foldamers: Ramping up diversity. Chem. Soc. Rev., 2012, 41, 687-702.
185. Menegazzo, I.; Fries, A.; Mammi, S.; Galeazzi, R.; Martelli, G.; Orena, M.; Rinaldi, S. Synthesis and structural characterization as 12-helix of the hex amer of a β-amino acid tethered to a pyrrolidin-2-one ring. Chem. Commun., 2006, (47), 4915-4917.
186. Galeazzi, R.; Martelli, G.; Mazzanti, A.; Orena, M.; Rinaldi, S. Quaternary centres as a tool for modulating foldamer conformation. Chem. Eur. J., 2011, 17, 12564-12568.