Examples of catalytic asymmetric amine synthesis using organic catalysts

Current Opinion in Drug Discovery and Development

Volumn 12, Issue 6, 2009, Pages 824-847

  Rios, Ramon ^a,b   Córdova, Armando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

3+2 cycloaddition; Aldehyde; Amino acid; Asymmetric catalysis; Aza Michael reaction; Chiral amine; Imine reduction; Ketone; Mannich reaction; Organocatalysis

Indexed keywords

AMINE; AMINO ACID; BETA AMINO ACID; IMINE; INCB 018424; JANUS KINASE INHIBITOR; PACLITAXEL; PYRROLIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; MANNICH REACTION; MICHAEL ADDITION; REVIEW;

AMINES; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; HYDROGENATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; STEREOISOMERISM;

EID: 70350751579     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (135)

1. Hajos ZG, Parrish DR: Asymmetric synthesis of bicyclic intermediates of natural product chemistry. J Org Chem (1974) 39(12):1615-1621.
2. Eder U, Sauer G, Wiechert R: New type of asymmetric cyclization to optically active steroid CD partial structures. Angew Chem Int Ed (1971) 10(7):496-497.
3. Woodward RB, Logusch E, Nambiar KP, Sakan K, Ward DE, Au-Yeung BW, Balaram P, Browne LJ, Card PJ, Chen CH: Asymmetric total synthesis of erythromycin. Synthesis of an erythronolide A secoacid derivative via asymmetric induction. J Am Chem Soc (1981) 103(11):3210-3213.
4. Kawara A, Taguxhi T: An enantioselective Michael addition of soft nucleophiles to prochiral enone catalyzed by (2-pyrrolidyl) alkyl ammonium hydroxide. Tetrahedron Lett (1994) 35(47): 8805-8808.
5. Paulmier C, Outurquin F, Plaquevent J-C: Enantioselective ?-selenenylation of 2-phenylpropanal. Tetrahedron Lett (1988) 29(46):5889-5891.
6. Noyori R: Asymmetric Catalysis in Organic Synthesis. Wiley, New York, NY, USA (1994).
7. Jacobsen EN, Pfaltz A, Yamamoto H (Eds): Comprehensive Asymmetric Catalysis. Springer, Berlin, Germany 1999).
8. Ojima I (Ed): Catalytic Asymmetric Synthesis, 2nd Edition. Wiley-VCH, New York, NY, USA (2000).
9. Roberts SM (Ed): Biocatalysts for Fine Chemicals Synthesis. Wiley-VCH, New York, NY, USA (1999).
10. Drauz K, Waldmann H (Eds): Enzyme Catalysis in Organic Synthesis 2nd Edition. Wiley-VCH, Weinheim, Germany 2002
11. Bommarius AS, Riebel BR: Biocatalysis. Wiley-VCH, Weinheim, Germany (2004).
12. List B, Lerner RA, Barbas CF 3rd: Proline-catalyzed direct asymmetric aldol reactions. J Am Chem Soc (2000) 122(10):2395-2396.
13. Ahrendt KA, Borths CJ, MacMillan DWC: New strategies for organic catalysis: The frst highly enantioselective organocatalytic Diels-Alder reaction. J Am Chem Soc (2000) 122(17):4243-4244.
14. Robinson R:LXIII-A synthesis of tropinone. J Chem Soc Trans (1917) 111:762-768.
15. Kleinmann EF: The biomolecular aliphatic Mannich and related reactions. In: Comprehensive Organic Synthesis. Trost BM, Fleming I (Eds), Pergamon Press, New York, NY, USA (1991) 2(Chapter 4.1):893-951.
16. Arend M, Westerman B, Risch N: Modern variants of the Mannich reaction. Angew Chem Int Ed (1998) 37(8):1044-1070.
17. Kobayashi S, Ishitani H: Catalytic enantioselective addition to imines. Chem Rev (1999) 99(5):1069-1094.
18. Denmark S, Nicaise OJ-C: Alkylation of imino groups. In: Comprehensive Asymmetric Catalysis. Jacobsen EN, Pfaltz A, Yamomoto H (Eds), Springer, Berlin, Germany (1999) 2(Chapter 26.2):923-961.
19. Juaristi E (Ed): Enantioselective Synthesis of p-Amino Acids. Wiley-VCH, New York, NY, USA (1997).
20. Córdova A: The direct catalytic asymmetric Mannich reaction. Acc Chem Res (2004) 37(2):102-112.
21. Ting A, Schaus SE: Organocatalytic asymmetric Mannich reactions: New methodology, catalyst design, and synthetic applications. Eur J Org Chem (2007) (35):5797-5815.
22. List B: The direct catalytic asymmetric three-component Mannich reaction. J Am Chem Soc (2000) 122(38):9336-9337.
23. List B, Porjalev P, Biller WT, Martin HJ: The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. J Am Chem Soc (2002) 124(5):827-833.
24. Notz W, Sakthivel K, Bui T, Zhong G, Barbas CF 3rd: Amine-catalyzed direct asymmetric Mannich-type reactions. Tetrahedron Lett (2001) 42(2):199-201.
25. Córdova A, Notz W, Zhong G, Betancort JM, Barbas CF 3rd: A highly enantioselective amino acid-catalyzed route to functionalized-amino acids. J Am Chem Soc (2002) 124(9): 1842-1843.
26. Córdova A, Watanabe S, Tanaka F, Notz W, Barbas CF 3rd: A highly enantioselective route to either enantiomer of both ex-and p-amino acid derivatives. J Am Chem Soc (2002) 124(9): 1866-1867.
27. Verkade JMM, Van Hemert LJC, Quaedfieg P, Schoemaker HE, Schürmann M, van Delft FL, Rutjes F: Laccase-mediated deprotection of para-methoxyphenyl (PMP)-protected amines. Adv Synth Catal (2007) 349(8-9):1332-1336.
28. Ibrahem I, Zou W, Engqvist M, Xu Y, Córdova A: Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. Chemistry (2005) 11(23):7024-7029.
29. Xu L-W, Luo J, Lu Y: Asymmetric catalysis with chiral primary amine-based organocatalysts. Chem Commun (2009) (14):1807-1821.
30. Ibrahem I, Casas J, Córdova A: Direct catalytic enantioselective-aminomethylation of ketones. Angew Chem Int Ed (2004) 43(47):6528-6531.
31. Ibrahem I, Zao W, Casas J, Sundén H, Córdova A: Direct organocatalytic enantioselective-aminomethylation of ketones. Tetrahedron (2005) 62(2-3):357-364.
32. Sundén H, Ibrahem I, Eriksson L, Córdova A: Direct catalytic enantioselective aza-Diels-Alder reactions. Angew Chem Int Ed (2005) 44(31):4877-4880.
33. Yamamoto Y, Momiyama N, Yamamoto H: Enantioselective tandem O-nitroso aldol/Michael reaction. J Am Chem Soc (2004) 126(19):5962-5963.
34. Córdova A: One-pot organocatalytic direct asymmetric synthesis of-amino alcohol derivatives. Synlett (2003) (11):1651-1654.
35. Córdova A: The direct catalytic asymmetric cross-Mannich reaction: A highly enantioselective route to 3-amino alcohols and ?-amino acid derivatives. Chemistry (2004) 10(8): 1987-1997.
36. Hayashi Y, Urushima T, Shoji M, Uchimaru T, Shiina I: The direct, enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes: The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions. Adv Synth Catal (2005) 347(11-13):1595-1604.
37. Chi Y, Gellman SH: Enantioselective organocatalytic aminomethylation of aldehydes: A role for ionic interactions and effcient access to ?2-amino acids. J Am Chem Soc (2006) 128(21):6804-6805.
38. Ibrahem I, Zhao G-L, Córdova A: Direct catalytic enantioselective ?-aminomethylation of aldehydes. Chemistry (2007) 13(2): 683-688.
39. Ibrahem I, Dziedzic P, Córdova A: Organocatalytic asymmetric ?-aminomethylation of cyclohexanones. Synthesis (2006) (23):4060-4064.
40. Enders D, Grondal C, Vrettou M, Raabe G: Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction. Angew Chem Int Ed (2005) 44(26):4079-4081.
41. Ibrahem I, Córdova A: Amino acid catalyzed direct enantio-selective formation of carbohydrates: One-step de novo synthesis of ketoses. Tetrahedron Lett (2005) 46(19):3363-3367.
42. Ibrahem I, Zou W-W, Xu Y, Córdova A: Amino acid-catalyzed asymmetric carbohydrate formation: Organocatalytic one-step de novo synthesis of keto and amino sugars. Adv Synth Catal (2006) 348(1-2):211-222.
43. Westermann B, Neuhaus C: Dihydroxyacetone in amino acid catalyzed Mannich-type reactions. Angew Chem Int Ed (2005) 44(26):4077-4079.
44. Enders D, Grondal C, Vrettou, M: Effcient entry to amino sugars and derivatives via asymmetric organocatalytic Mannich reactions. Synthesis (2006) (21):3597-3604.
45. Liao W-W, Ibrahem I, Córdova A: A concise enantioselective synthesis of iminosugar derivatives. Chem Commun (2006) (6):674-677.
46. Vesely J, Rios R, Ibrahem I, Córdova A: Highly enantioselective organocatalytic addition of unmodifed aldehydes to N-Boc protected imines: One-pot asymmetric synthesis of ?-amino acids. Tetrahedron Lett (2007) 48(3):421-425. (Pubitemid 44894507)
47. Yang JW, Stadler M, List B: Proline-catalyzed Mannich reaction of aldehydes with N-Boc-imines. Angew Chem Int Ed (2007) 46(4):609-611.
48. Yang JW, Chandler C, Stadler M, Kampen D, List B: Proline-catalysed Mannich reactions of acetaldehyde. Nature (2008) 452(7186):453-455.
49. Dziedzic P, Vesely J, Córdova A: Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: Organocatalytic highly enantioselective synthesis of esterifcation-ready ?-hydroxy-?-amino acids. Tetrahedron Lett (2008) 49(47): 6631-6634.
50. Valero G, Balaguer A-N, Moyano A, Rios R: Enantioselective organocatalytic Mannich reactions of ferrocenecarbaldehyde Tetrahedron Lett (2008) 49(46):6559-6562.
51. Dziedzic P, Schyman P, Kullberg M, Córdova A: Highly enantio-selective organocatalytic addition of aldehydes to N-(phenylmethylene) benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues. Chemistry (2009) 15(16):4044-4048.
52. Mitsumori S, Zhang H, Cheong PH-Y, Houk KN, Tanaka F, Barbas CF 3rd: Direct asymmetric anti-Mannich-type reactions catalyzed by a designed amino acid. J Am Chem Soc (2006) 128(4):1040-1041.
53. Zhang H, Misfud M, Tanaka F, Barbas CF 3rd: 3-Pyrrolidine-carboxylic acid for direct catalytic asymmetric anti-Mannich-type reactions of unmodifed ketones. J Am Chem Soc (2006) 128(30):9630-9631.
54. Kano T, Yamaguchi Y, Tokuda O, Maruoka K: Anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst. J Am Chem Soc (2005) 127(47):16408-16409. (Pubitemid 41740387)
55. Kano T, Hato Y, Maruoka K: Design of a C2-symmetric chiral pyrrolidine-based amino sulfonamide: Application to anti-selective direct asymmetric Mannich reactions. Tetrahedron Lett (2006) 47(48):8467-8470.
56. Ibrahem I, Córdova A: Direct catalytic asymmetric anti-selective Mannich-type reactions. Chem Commun (2006) (16):1760-1762. (Pubitemid 43793263)
57. Franzén J, Marigo M, Fielenbach D, Wabniz TC, Kjaergaard A, Jørgensen KA: A general organocatalyst for direct ?-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights. J Am Chem Soc (2005) 127(51):18296-18304.
58. Uraguchi D, Terada M: Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. J Am Chem Soc (2004) 126(17):5356-5357.
59. Akiyama T, Itoh J, Yokota K, Fuchibe K: Enantioselective Mannich-type reaction catalyzed by a chiral Brønsted acid. Angew Chem Int Ed (2004) 43(12):1566-1568.
60. Akiyama T, Morita H, Fuchibe K: Chiral Brønsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction. J Am Chem Soc (2006) 128(40):13070-13071.
61. Itoh J, Fuchibe K, Akiyama T: Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines. Angew Chem Int Ed (2006) 45(29):4796-4798. (Pubitemid 44179117)
62. Rueping M, Azap C: Cooperative coexistence: Effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines. Angew Chem Int Ed (2006) 45(46):7832-7835.
63. Liu H, Cun L-F, Mi A-Q, Jiang Y-Z, Gong L-Z: Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids. Org Lett (2006) 8(26):6023-6025.
64. Yoon TP, Jacobsen EN: Highly enantioselective thiourea-catalyzed nitro-Mannich reactions. Angew Chem Int Ed (2005) 44(3):466-468.
65. Fini F, Sgarzani V, Pettersen D, Herrera RP, Bernardi L, Ricci A: Phase-transfer-catalyzed asymmetric aza-Henry reaction using N-carbamoyl imines generated in situ from ?-amido sulfones. Angew Chem Int Ed (2005) 44(48):7975-7978.
66. Hortsmann TE, Guerin DJ, Miller SJ: Asymmetric conjugate addition of azide to ?,?-unsaturated carbonyl compounds catalyzed by simple peptides. Angew Chem Int Ed (2000) 39(20):3635-3639.
67. Chen YK, Yoshida M, MacMillan DW: Enantioselective organocatalytic amine conjugate addition. J Am Chem Soc (2006) 128(29):9328-9329.
68. Vesely J, Ibrahem I, Rios R, Zhao G-L, Xu Y, Córdova A: Enantioselective organocatalytic conjugate addition of amines to ?,?-unsaturated aldehydes: One-pot asymmetric synthesis of ?-amino acids and 1,3-diamines. Tetrahedron Lett (2007) 48(12):2193-2198. (Pubitemid 46275847)
69. Ibrahem I, Rios R, Vesely J, Zhao G-L, Córdova A: Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: A highly enantioselective route to ?-amino acids. Chem Commun (2007) (8):849-851. (Pubitemid 46272163)
70. Sundén H, Rios R, Ibrahem I, Zhao G-L, Eriksson L, Córdova A: A highly enantioselective catalytic domino aza-Michael/aldol reaction: One-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolines. Adv Synth Catal (2007) 349(6):827-832.
71. Li H, Wang J, Xie H, Zu L, Jian W, Duesler EN, Wang W: Chiral diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between ?,?-unsaturated aldehydes and 2-N-protected amino benzaldehydes. Org Lett (2007) 9(6):965-968.
72. Vesely J, Ibrahem I, Zhao G-L, Rios R, Córdova A: Organocatalytic enantioselective aziridination of ?,?-unsaturated aldehydes. Angew Chem Int Ed (2007) 46(5):778-781. (Pubitemid 46155410)
73. Deiana L: Investigation of the organocatalytic asymmetric aziridination of ?,?-unsaturated aldehydes. Diploma Thesis, Stockholm University, Department of Organic Chemistry, Stockholm, Sweden (2009).
74. Arai H, Sugaya N, Sasaki N, Makino K, Lectard S, Hamada Y: Enantioselective aziridination reaction of ?,?-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates. Tetrahedron Lett (2009) 50(26):3329-3332.
75. Pesciaioli F, De Vincentis F, Galzerano P, Bencivenni G, Bartoli G, Mezzanti A, Mechiorre P: Organocatalytic asymmetric aziridination of enones. Angew Chem Int Ed (2008) 47(45):8703-8706.
76. Li H, Zu L, Xie H, Wang J, Wang W: Highly enantio-and diastereoselective organocatalytic cascade aza-Michael-Michael reactions: A direct method for the synthesis of trisubstituted chiral pyrrolidines. Chem Commun (2008) (43):5636-5638.
77. Fustero S, Jimenez D, Moscardó J, Catalán S, del Pozo C: Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine. Org Lett (2007) 9(25):5283-5286.
78. Fustero S, Moscardó J, Jimenez D, Perez-Carrión MD, Sánchez-Rosselló M, del Pozo C: Organocatalytic approach to benzofused nitrogen-containing heterocycles: Enantioselective total synthesis of (+)-angustureine. Chemistry (2008) 14(32):9868-9872.
79. Zhao G-L, Rios R, Vesely J, Eriksson L, Córdova A: Organocatalytic enantioselective aminosulfenylation of ?,?-unsaturated aldehydes. Angew Chem Int Ed (2008) 47(44):8468-8472.
80. Lin G, Meloni D, Pan Y, Xia M, Rodgers J, Shepard S, Li M, Galya L, Metcalf B, Yue T-Y, Liu P et al: Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction. Org Lett (2009) 11(9):1999-2002.
81. Uria U, Vicario J, Badia D, Carrillo L: Organocatalytic enantioselective aza-Michael reaction of nitrogen heterocycles and ?,?-unsaturated aldehydes. Chem Commun (2007) (24):2509-2511. (Pubitemid 46906708)
82. Dinér P, Nielsen M, Marigo M, Jørgensen KA: Enantioselective organocatalytic conjugate addition of N-heterocycles to ?,?-unsaturated aldehydes. Angew Chem Int Ed (2007) 46(12):1983-1987.
83. Perdicchia D, Jørgensen KA: Asymmetric aza-Michael reactions catalyzed by cinchona alkaloids. J Org Chem (2007) 72(9):3565-3568.
84. Lu X, Deng L: Asymmetric aza-Michael reactions of ?,?-unsaturated ketones with bifunctional organic catalysts. Angew Chem Int Ed (2008) 47(40):7710-7713.
85. Gogoi S, Zhao C-G, Ding D: Enantioselective synthesis of ?-(3-hydroxypyrazol-1-yl) ketones using an organocatalyzed Michael addition reaction. Org Lett (2009) 11(11):2249-2252.
86. Vicario J, Reboredo S, Badía D, Carrillo L: Organocatalytic enantioselective [3+2] cycloaddition of azomethine ylides and ?,?-unsaturated aldehydes. Angew Chem Int Ed (2007) 46(27):5168-5170. (Pubitemid 47053850)
87. Ibrahem I, Rios R, Vesely J, Córdova A: Organocatalytic asymmetric multi-component [C+NC+CC] synthesis of highly functionalized pyrrolidine derivatives. Tetrahedron Lett (2007) 48(36):6252-6257. (Pubitemid 47211237)
88. Guo C, Xue M-X, Zhu M-K, Gong L-Z: Organocatalytic asymmetric formal [3+2] cycloaddition reaction of isocyanoesters to nitroolefns leading to highly optically active dihydropyrroles. Angew Chem Int Ed (2008) 47(18):3414-3417.
89. Xue M-X, Zhang X-M, Gong L-Z: The frst organocatalytic enantio-and diastereoselective 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes. Synlett (2008) (5): 691-694.
90. Crovetto L, Rios R: One-pot, three-component, highly diastereoselective metal-free synthesis of 2,3,4,5-tetrasubstituted pyrrolidines. Synlett (2008) 5:1840-1844.
91. Liu Y-K, Liu H, Du W, Yue L, Chen Y-C: Reaction control in the organocatalytic asymmetric one-pot, three-component reaction of aldehydes, diethyl ?-aminomalonate and nitroalkenes: Toward diversity-oriented synthesis. Chemistry (2008) 14(32):9873-9877.
92. Xie J, Yoshida K, Takasu K, Takemoto Y: Thiourea-catalyzed asymmetric formal [3+2] cycloaddition of azomethine ylides with nitroolefns. Tetrahedron Lett (2008) 49(48):6910-6913.
93. Chen X-C, Zgang W-Q, Gong L-Z: Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: Control of stereochemistry via a chiral Brønsted acid activated dipole. J Am Chem Soc (2008) 130(17):5652-5653.
94. Rueping M, Sugiono E, Azap C, Thiessmann T, Bolte M: Enantioselective Brønsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines. Org Lett (2005) 7(17):3781-3783.
95. Hoffmann S, Seayad AM, List B: A powerful Brønsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines. Angew Chem Int Ed (2005) 44(45):7424-7427.
96. Storer RI, Carrera DE, Ni Y, MacMillan DW: Enantioselective organocatalytic reductive amination. J Am Chem Soc (2006) 128(1):84-86.
97. Hoffmann S, Nicoletti M, List B: Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution. J Am Chem Soc (2006) 128(40):13074-13075.
98. Iwasaki F, Omonura O, Mishima K, Kanematsu T, Maki T, Matsumura Y: First chemo-and stereoselective reduction of imines using trichlorosilane activated with N-formylpyrrolidine derivatives. Tetrahedron Lett (2001) 42(13):2525-2527.
99. Malkov AV, Mariani A, MacDougall KN, Kocovsky P: Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane. Org Lett (2004) 6(13):2253-2256.
100. Malkov AV, Stoncious S, MacDougall KM, Mariani A, McGeoch GD, Kocovsky P: Formamides derived from N-methyl aminoacids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane. Tetrahedron (2006) 62(2-3):264-284.
101. Malkov AV, Liddon AJ, Ramírez-López P, Bendová L, Haigh D, Kocovský P: Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines. Angew Chem Int Ed (2006) 45(9):1432-1435.
102. Malkov AV, Figlus M, Cooke G, Caldwell ST, Rabani G, Prestly MR, Kocovsky P: Organocatalysts immobilized onto gold nanoparticles: Application in the asymmetric reduction of imines with trichlorosilane. Org Biomol Chem (2009) 7(9): 1878-1883.
103. Malkov AV, Figlus M, Stoncius S, Kocovsky P: Organocatalysis with a fuorous Tag: Asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides. J Org Chem (2007) 72(4):1315-1325.
104. Malkov AV, Stoncius S, Kocovský P: Enantioselective synthesis of 1,2-diarylaziridines by the organocatalytic reductive amination of-chloroketones. Angew Chem Int Ed (2007) 46(20):3722-3724.
105. Malkov AV, Stoncius S, Vranková K, Arndt M, Kocovský P: Dynamic kinetic resolution in the asymmetric synthesis of-amino acids by organocatalytic reduction of enamines with trichlorosilane. Chemistry (2008) 14(27):8082-8085.
106. Gautier F-M, Jones S, Martin SJ: Asymmetric reduction of ketimines with trichlorosilane employing an imidazole derived organocatalyst. Org Biomol Chem (2009) 7(2):229-231.
107. Bogevig A, Juhl K, Kumaragurubaran N, Zhuang W, Jørgensen KA: Direct organo-catalytic asymmetric-amination of aldehydes-A simple approach to optically active-amino aldehydes,-amino alcohols, and-amino acids. Angew Chem Int Ed (2002) 41(10):1790-1793.
108. List B: Direct catalytic asymmetric-amination of aldehydes. J Am Chem Soc (2002) 124(20):5656-5657.
109. Kumaragurubaran N, Juhl K, Zhuang W, Bøgevig A, Jørgensen KA: Direct L-proline-catalyzed asymmetric-amination of ketones. J Am Chem Soc (2002) 124(22):6254-6255.
110. Bertelsen S, Marigo M, Brandes S, Dinér P, Jørgensen KA: Dienamine catalysis: Organocatalytic asymmetric-amination of,|-unsaturated aldehydes. J Am Chem Soc (2006) 128(39):12973-12980.
111. Okino T, Hoashi Y, Takemoto Y: Enantioselective Michael reaction of malonates to nitroolefns catalyzed by bifunctional organocatalysts. J Am Chem Soc (2003) 125(42):12672-12673.
112. Hoashi Y, Yabuta T, Yuan P, Miyabe H, Takemoto Y: Enantioselective tandem Michael reaction to nitroalkene catalyzed by bifunctional thiourea: Total synthesis of (-)-epibatidine. Tetrahedron (2006) 62(2-3):365-374.
113. He M, Struble JR, Bode JW: Highly enantioselective azadiene Diels-Alder reactions catalyzed by chiral N-heterocyclic carbenes. J Am Chem Soc (2006) 128(26):8418-8420.
114. Seayad J, Seayad AM, List B: Catalytic asymmetric Pictet-Spengler reaction. J Am Chem Soc (2006) 128(4):1086-1087.
115. Rueping M, Antonchick AP, Theissmann T: A highly enantioselective Brønsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids. Angew Chem Int Ed (2006) 45(22):3683-3686.
116. Zhou J, List B: Organocatalytic asymmetric reaction cascade to substituted cyclohexylamines. J Am Chem Soc (2007) 129(24):7498-7499.
117. Zhou J, List B: Synthesis of trans-3-substituted cyclohexylamines via Brønsted acid catalyzed and substrate-mediated triple organocatalytic cascade reaction. Synlett (2007) (13):2037-2040.
118. Terada M, Machioka K, Sorimachi K: Chiral Brønsted acid-catalyzed tandem aza-ene type reaction/cyclization cascade for a one-pot entry to enantioenriched piperidines. J Am Chem Soc (2007) 129(34):10336-10337.
119. Rios R, Ibrahem I, Vesely J, Córdova A: Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis: A highly enantioselective route to 3-substituted proline derivatives. Tetrahedron Lett (2007) 48(49):8695-8699. (Pubitemid 350046788)
120. Franzén J, Fisher A: Asymmetric alkaloid synthesis: A one-pot organocatalytic reaction to quinolizidine derivatives. Angew Chem Int Ed (2009) 48(4):787-791.
121. Valero G, Schimer J, Cisarova I, Vesely J, Moyano A, Rios R: Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-paroxetine. Tetrahedron Lett (2009) 50(17):1943-1946.
122. Han B, Li J-L, Ma C, Zhang S-J, Chen Y-C: Organocatalytic asymmetric inverse-electron-demand aza-Diels-Alder reaction of N-sulfonyl-1-aza-1,3- butadienes and aldehydes. Angew Chem Int Ed (2008) 47(51):9971-9974.
123. Rueping M, Antonchick AP: A highly enantioselective Brønsted acid catalyzed reaction cascade. Angew Chem Int Ed (2008) 47(31):5836-5838.
124. Pan SC, List B: The catalytic acylcianation of imines. Chem Asian J (2008) 3:430-437.
125. Reingruber R, Baumann T, Dahmen S, Bräse S: Use of the chiral pool-Practical asymmetric organocatalytic Strecker reaction with quinine. Adv Synth Catal (2009) 351(7-8):1019-1024.
126. Hou Z, Wang J, Liu X, Feng X: Highly enantioselective Strecker reaction of ketoimines catalyzed by an organocatalyst from (S)-BINOL and l-prolinamide. Chemistry (2008) 14(15):4484-4486.
127. Wang X, Chen Y-F, Niu L-F, Xu P-F: Diastereo-and enantioselective aza-MBH-type reaction of nitroalkenes to N-tosylimines catalyzed by bifunctional organocatalysts. Org Lett (2009) 11(15):3310-3313.
128. He L, Zhang Y-R, Huang X-L, Ye S: Chiral bifunctional N-heterocyclic carbenes: Synthesis and application in the aza-Morita-Baylis-Hillman reaction. Synthesis (2008) 17:2825-2829.
129. Vesely J, Dziedzic P, Córdova A: Aza-Morita-Baylis-Hillman-type reactions: Highly enantioselective organocatalytic addition of unmodifed aldehydes to N-Boc protected imines. Tetrahedron Lett (2007) 48(39):6900-6904. (Pubitemid 47331559)
130. Shi Y-L, Shi M: Chiral thiourea-phosphine organocatalysts in the asymmetric aza-Morita-Baylis-Hillman reaction. Adv Synth Catal (2007) 349(13):2129-2135.
131. Matsui K, Takizawa S, Sasai H: Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction. J Am Chem Soc (2005) 127(11):3680-3681.
132. Uraguchi D, Sorimachi K, Terada M: Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan. J Am Chem Soc (2004) 126(38):11804-11805.
133. Kang Q, Zhao Z-A: You S-L: Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid. J Am Chem Soc (2007) 129(6):1484-1485.
134. Wang Y-Q, Song J, Hong R, Li H, Deng L: Asymmetric Friedel-Crafts reaction of indoles with imines by an organic catalyst. J Am Chem Soc (2006) 128(25):8156-8157.
135. Li G, Rowland GB, Rowland EB, Antilla JC: Organocatalytic enantioselective Friedel-Crafts reaction of pyrrole derivatives with imines. Org Lett (2007) 9(20):4065-4068.