Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2012; 23(8): 1108-1131
DOI: 10.1055/s-0031-1290193
DOI: 10.1055/s-0031-1290193
account
Organocatalytic Asymmetric Hydrophosphonylation/Mannich Reactions Using Thiourea, Cinchona and Brønsted Acid Catalysts
Further Information
Publication History
Received: 11 October 2011
Accepted after revision: 13 December 2011
Publication Date:
23 April 2012 (online)
Dedicated to Anupa Bhadury on the occasion of her 45th birthday.
Abstract
This account summarizes the results of recent studies conducted in our group on the development of chiral thiourea/cinchona and Brønsted acid derived bifunctional organocatalysts. Selected asymmetric organocatalytic transformations were targeted to obtain enantioenriched bioactive products. Special emphasis was placed on the preparation of environmentally friendly anti-plant viral agents such as enantiomerically enriched α-aminophosphonates and methods to assess the enantiomeric purity of these products on selected chiral stationary phases. The review also tries to delineate the underlying mechanism of various asymmetric transformations by BINOL-phosphoric acid-induced activation of imines and to make unambiguous assignments of the absolute configuration of α-aminophosphonates obtained from organocatalytic hydrophosphonylation of pregenerated and in situ generated imines.
1 Introduction
2 BINOL-Derived Brønsted Acid Organocatalysts and Their Applications
2.1 Two-Component Reaction
2.2 Three-Component Reaction
2.3 Analytical Aspects
2.4 Absolute Configuration and Proposed Mechanism
3 Chiral Thiourea/Cinchona Derived Bifunctional Organocatalysts and Their Applications
4 Ongoing Activities
5 Concluding Remarks
-
References
- 1 Bhadury PS, Song BA, Yang S, Zhang YP, Zhang S. Curr. Org. Synth. 2008; 5: 134
- 2 Bhadury PS, Song BA, Yang S, Hu DY, Xue W. Curr. Org. Synth. 2009; 6: 380
- 3 Bhadury PS, Song BA. Curr. Org. Chem. 2010; 14: 1989
- 4 Bhadury PS, Yang S, Song BA. Curr. Org. Synth. 2012; 9: DOI: 102174/1570212700121031794
- 5 Bhadury PS, Zhang Y, Zhang S, Song BA, Yang S, Hu DY, Chen Z, Xue W, Jin LH. Chirality 2009; 21: 547
- 6 Zhou SL, Fleischer S, Junge K, Beller M. Angew. Chem. Int. Ed. 2011; 50: 5120
- 7 Barbero M, Bazzi S, Cadamuro S, Dughera S, Magistris C, Smarra A, Venturello P. Org. Biomol. Chem. 2011; 9: 2192
- 8 Naziroglu HN, Durmaz M, Bozkurt S, Sirit A. Chirality 2011; 23: 463
- 9 Blackmond DG, Moran A, Hughes M, Armstrong A. J. Am. Chem. Soc. 2010; 132: 7598
- 10 Schenker S, Zamfir A, Freund M, Tsogoeva SB. Eur. J. Org. Chem. 2011; 2209
- 11 Zhang T, Cheng L, Hameed S, Liu L, Wang D, Chen YJ. Chem. Commun. 2011; 47: 6644
- 12 Yamanaka M, Itoh J, Fuchibe K, Akiyama T. J. Am. Chem. Soc. 2007; 129: 6756
- 13 Guo QX, Liu H, Guo C, Luo SW, Gu Y, Gong LZ. J. Am. Chem. Soc. 2007; 129: 3790
- 14 Rueping M, Antonchick AP. Angew. Chem. Int. Ed. 2007; 46: 4562
- 15 Ii GL, Liang YX, Antilla JC. J. Am. Chem. Soc. 2007; 129: 5830
- 16 Akiyama T, Morita H, Itoh J, Fuchibe K. Org. Lett. 2005; 7: 2583
- 17 Seayad J, Seayad AM, List B. J. Am. Chem. Soc. 2006; 128: l086
- 18 Rueping M, SuNono E, Azap C. Angew. Chem. Int. Ed. 2006; 45: 2617
- 19 Rowland GB, Zhang H, Rowland EB, Chennamadhavuni S, Wang Y, Antilla JC. J. Am. Chem. Soc. 2005; 127: 15696
- 20 Chen XH, Xu XY, Liu H, Cun LF, Gong LZ. J. Am. Chem. Soc. 2006; 128: 14802
- 21 Rowland GB, Rowland EB, Liang YX, Perman JA, Antilla JC. Org. Lett. 2007; 9: 2609
- 22 Jia YX, Zhong J, Zhu SF, Zhang CM, Zhou QL. Angew. Chem. Int. Ed. 2007; 46: 5565
- 23 Akiyama T, Morita H, Fuchibe K. J. Am. Chem. Soc. 2006; 128: 13070
- 24 Rueping M, Azap C. Angew. Chem. Int. Ed. 2006; 45: 832
- 25 Teradan M, Maehioka K, Sofimaehi K. Angew. Chem. Int. Ed. 2006; 45: 2254
- 26 Uraguchi D, Sofimaehi K, Terada M. J. Am. Chem. Soc. 2005; 127: 9360
- 27 Xu GF, Song BA, Bhadury PS, Yang S, Zhang PQ, Jin LH, Xue W, Hu DY, Lu P. Bioorg. Med. Chem. 2007; 15: 3768
- 28 Chen CJ, Song BA, Yang S, Xu GP, Bhadury PS, Jin LH, Hu DY, Li QZ, Liu F, Xue W, Lu P, Chen Z. Bioorg. Med. Chem. 2007; 15: 3981
- 29 Liu G, Hu DY, Jin LH, Song BA, Yang S, Bhadury PS, Ma Y, Luo H, Zhou X. Bioorg. Med. Chem. 2007; 15: 6608
- 30 Liu XH, Song BA, Bhadury PS, Zhu HL, Cui P, Hou KK, Xu HL. Aust. J. Chem. 2008; 61: 864
- 31 Ouyang GP, Cai XJ, Chen Z, Song BA, Bhadury PS, Yang S, Jin LH, Xue W, Hu DY, Zeng S. J. Agric. Food Chem. 2008; 56: 10160
- 32 Ouyang GP, Chen Z, Cai XJ, Song BA, Bhadury PS, Yang S, Jin LH, Xue W, Hu DY, Zeng S. Bioorg. Med. Chem. 2008; 16: 9699
- 33 Liu F, Luo XQ, Song BA, Bhadury PS, Yang S, Jin LH, Xue W, Hu DY. Bioorg. Med. Chem. 2008; 16: 3632
- 34 Liu XH, Cui P, Song BA, Bhadury PS, Zhu HL, Wang SF. Bioorg. Med. Chem. 2008; 16: 4075
- 35 Chen Z, Liu YM, Yang S, Song BA, Xu GF, Bhadury PS, Jin LH, Hu DY, Liu F, Xue W, Zhou X. Bioorg. Med. Chem. 2008; 16: 1337
- 36 Wu Q, Song BA, Yang S, Bhadury PS, Hu DY, Xue W, Jin LH, Chen Z. Chin. J. Chem. 2008; 26: 1327
- 37 Wu J, Song BA, Chen HG, Bhadury PS, Hu DY. Molecules 2009; 14: 3676
- 38 Liu XH, Zhu J, Zhou AN, Song BA, Zhu HL, Bai LS, Bhadury PS, Pan CX. Bioorg. Med. Chem. 2009; 17: 1207
- 39 Song BA, Yang S, Jin LH, Bhadury PS. Environment-Friendly Antiviral Agents for Plants. Springer; Berlin; jointly published with Chemical Industry Press: China: 2010
- 40 Xu WM, Song BA, Bhadury PS, Yang S, Hu DY. Molecules 2010; 15: 766
- 41 Yang JQ, Song BA, Bhadury PS, Chen Z, Yang S, Cai XJ, Hu DY, Xue W. J. Agric. Food Chem. 2010; 58: 2730
- 42 Liu XH, Liu HF, Shen X, Song BA, Bhadury PS, Zhu HL, Liu JX, Qi XB. Bioorg. Med. Chem. Lett. 2010; 20: 4163
- 43 Chen Z, Xu WM, Liu K, Yang S, Fan H, Bhadury PS, Huang DY, Zhang Y. Molecules 2010; 15: 9046
- 44 Wu LT, Song BA, Bhadury PS, Yang S, Hu DY, Jin LH. J. Heterocycl. Chem. 2011; 48: 389
- 45 Wu J, Yang S, Song BA, Bhadury PS, Hu DY, Zeng S, Xie HP. J. Heterocycl. Chem. 2011; 48: 901
- 46 Hu DY, Wan QQ, Yang S, Song BA, Bhadury PS, Jin LH, Yan K, Liu F, Chen Z, Xue W. J. Agric. Food Chem. 2008; 56: 998
- 47 Zhou J, Fan HT, Song BA, Jin LH, Bhadury PS, Hu DY, Yang S. Phosphorus, Sulfur Silicon Relat. Elem. 2011; 186: 81
- 48 Yan ZK, Cai XJ, Yang X, Song BA, Chen Z, Bhadury PS, Hu DY, Jin LH, Xue W, Lu P. Chin. J. Chem. 2009; 27: 593
- 49 Chen MH, Chen Z, Song BA, Bhadury PS, Yang S, Cai XJ, Hu DY, Xue W, Zeng S. J. Agric. Food Chem. 2009; 57: 1383
- 50 Liu JZ, Song BA, Fan HT, Bhadury PS, Wan WT, Yang S, Xu WM, Wu J, Jin LH, Xue W, Hu DY, Zeng S. Eur. J. Med. Chem. 2010; 45: 5108
- 51 Liu JZ, Yang S, Li X, Fan H, Bhadury PS, Xu W, Wu J, Wang Z. Molecules 2010; 15: 5112
- 52 Yang X, Song BA, Jin LH, Xue W, Bhadury PS, Li XY, Yang S, Hu DY. Sci. China Chem. 2011; 54: 103
- 53 Lv YP, Wang XY, Song BA, Yang S, Yan K, Xu GF, Bhadury PS, Liu F, Jin LH, Hu DY. Molecules 2007; 12: 965
- 54 Long N, Cai XJ, Song BA, Yang S, Chen Z, Bhadury PS, Hu DY, Jin LH, Xue W. J. Agric. Food Chem. 2008; 56: 5242
- 55 Fan HT, Song BA, Bhadury PS, Jin LH, Hu DY, Yang S. Int. J. Mol. Sci. 2011; 12: 4522
- 56 Giera DS, Sickert M, Schneider C. Org. Lett. 2008; 10: 4259
- 57 DeBerardinis AM, Turlington M, Ko J, Sole L, Pu L. J. Org. Chem. 2010; 75: 2836
- 58 Xu FX, Huang D, Han C, Shen W, Lin XF, Wang YG. J. Org. Chem. 2010; 75: 8677
- 59 Akiyama T, Itoh J, Fuchibe K. Angew. Chem. Int. Ed. 2006; 45: 4796
- 60 Li N, Chen XH, Song J, Luo SW, Fan W, Gong LZ. J. Am. Chem. Soc. 2009; 131: 15301
- 61 Troyer TL, Muchalski H, Hong KB, Johnston JN. Org. Lett. 2011; 13: 1790
- 62 Ordóñez M, Cabrera HR, Cativiela C. Tetrahedron 2009; 65: 17
- 63 Akiyama T, Morita H, Bachu P, Mori K, Yamanaka M, Hirata T. Tetrahedron 2009; 65: 4950
- 64 Zhang GP, Song BA, Xue W, Jin LH, Hu DY, Wan QQ, Lu P, Yang S, Li QZ, Liu G. J. Fluorine Chem. 2006; 127: 48
- 65 Xu YS, Yan K, Song B.-A, Xu G.-F, Yang S, Xue W, Hu DY, Lu P, Ouyang GP, Jin LH, Chen Z. Molecules 2006; 11: 666
- 66 Song BA, Wu YL, Yang S, Hu DY, He XQ, Jin LH. Molecules 2003; 8: 186
- 67 Enders D, Tedeshi L, Bats JW. Angew. Chem. Int. Ed. 2000; 39: 4605
- 68 Davis FA, Lee S, Yan H, Titus DD. Org. Lett. 2001; 3: 1757
- 69 Palacios F, Alonso C, Santos JM. D. L. Chem. Rev. 2005; 105: 899
- 70 Gröger H, Hammer B. Chem. Eur. J. 2000; 6: 943
- 71 Gröger H, Saida Y, Sasai H, Yamaguchi K, Martens J, Shibasaki M. J. Am. Chem. Soc. 1998; 120: 3089
- 72 Kobayashi S, Kiyohara H, Nakamura Y, Matsubara RJ. J. Am. Chem. Soc. 2004; 126: 6558
- 73 Joly GD, Jacobsen EN. J. Am. Chem. Soc. 2004; 126: 4102
- 74 Pettersen D, Marcolini M, Bernardi L, Fini F, Herrera RP, Sgarzani V, Ricci A. J. Org. Chem. 2006; 71: 6269
- 75 Uraguchi D, Tereda M. J. Am. Chem. Soc. 2004; 126: 5356
- 76 Storer RI, Carrera DE, Ni Y, MacMillan DW. C. J. Am. Chem. Soc. 2006; 128: 84
- 77 Simonsen KB, Gothelf KV, Jørgensen KA. J. Org. Chem. 1998; 63: 7536
- 78 Wipf P, Jung JK. J. Org. Chem. 2000; 65: 6319
- 79 Wang Y, Fang X, Ye W, Lou A. J. Cent. China Normal Univ. 1995; 29: 55
- 80 Xu WM, Zhang S, Yang S, Jin LH, Bhadury PS, Hu DY, Zhang Y. Molecules 2010; 15: 5782
- 81 Bai S, Song BA, Bhadury PS, Yang S, Hu DY, Xue W. Chin. J. Chem. 2011; 29: 109
- 82 Cheng X, Goddard R, Buth G, List B. Angew. Chem. Int. Ed. 2008; 47: 5079
- 83 Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS. Nature 1979; 272: 565
- 84 Atherton FR, Hall MJ, Hassel CH, Lambert RW, Lloyd WY, Ringrose PS. Antimicrob. Agents Chemother. 1979; 15: 677
- 85 Carmela D, Daiela P, Alessandro D, Gianpiero P, Valerio B. Eur. J. Org. Chem. 2003; 1904
- 86 Berlicki L, Rudzińska E, Mucha A, Kafarski P. Tetrahedron: Asymmetry 2004; 15: 1597
- 87 Berlicki L, Rudzińska E, Kafarski P. Tetrahedron: Asymmetry 2003; 14: 1535
- 88 Okamoto Y, Kaida Y. J. Chromatogr., A 1994; 666: 403
- 89 Lámmerhofer M, Hebenstreit D, Gavioli E, Lindner W, Mucha A, Kafarski P, Wieczorek P. Tetrahedron: Asymmetry 2003; 14: 2557
- 90 Kee TP, Nixon TD. Top. Curr. Chem. 2002; 223: 45
- 91 Rudzińska E, Dzygiel P, Wieczorek P, Kafarski P. J. Chromatogr., A 2002; 979: 115
- 92 Pirkle WH, Brice LJ, Caccumese S, Principato G, Failla S. J. Chromatogr., A 1996; 721: 241
- 93 Zhou AL, Lu XY, Chao Y, Gao RY. Anal. Chim. Acta 2005; 547: 158
- 94 Zhou AL, Wang XL, Huang JM, Wang XS, Gao RY. Chem. J. Chin. Univ. 2003; 24: 1610
- 95 Chen H, Lü XY, Huang JM, Gao RY, Wang QS. Chem. J. Chin. Univ. 2000; 21: 562
- 96 Song BA, Hong YP, Jin LH, Yang S, Zou ZH, Hu DY, He W, Liu G, Zhang GP, Li QZ. Chin. J. Org. Chem. 2005; 25: 1001
- 97 Jin LH, Song BA, Zhang GP, Xu RQ, Zhang SM, Gao XW, Hu DY, Yang S. Bioorg. Med. Chem. Lett. 2006; 16: 1537
- 98 Yang S, Song BA, Wu YL, Jin LH, Liu G, Hu DY, Lu P. Chin. J. Org. Chem. 2004; 24: 1292
- 99 Lu P, Zhang YP, Song BA, Yang S, Bhadury PS, Hu DY, Xue W, Chen Z, Jin LH. Chin. J. Chem. 2008; 26: 1659
- 100 Zhang YP, Song BA, Bhadury PS, Hu DY, Yang S, Shi X, Liu DM, Jin LH. J. Sep. Sci. 2008; 31: 2946
- 101 Zhang YP, Hang XY, Zhou J, Song BA, Bhadury PS, Hu DY, Yang S. J. Sep. Sci. 2011; 34: 402
- 102 Simon L, Goodman JM. J. Org. Chem. 2011; 76: 1775
- 103 Fleischmann M, Drettwan D, Sugiono E, Rueping M, Gschwind RM. Angew. Chem. Int. Ed. 2011; 50: 6364
- 104 Husmann R, Sugiono E, Mersmann S, Raabe G, Rueping M, Bolm C. Org. Lett. 2011; 13: 1044
- 105 Lu GJ, Birman VB. Org. Lett. 2011; 13: 356
- 106 Johnston JN. Angew. Chem. Int. Ed. 2011; 50: 2890
- 107 Rueping M, Nachtsheim BJ, Ieawsuwan W, Atodiresei I. Angew. Chem. Int. Ed. 2011; 50: 6706
- 108 Okino T, Hoashi Y, Takemoto Y. J. Am. Chem. Soc. 2003; 125: 12672
- 109 Sohtome Y, Tanatani A, Hashimoto Y, Nagasawa K. Tetrahedron Lett. 2004; 45: 5589
- 110 Sohtome Y, Hashimoto Y, Nagasawa K. Adv. Synth. Catal. 2005; 347: 1643
- 111 Herrera RP, Sqarzani V, Bernardi L, Ricci A. Angew. Chem. Int. Ed. 2005; 44: 6576
- 112 Yuan XY, Li HY, Hodge F, Kilner M, Tastard CY, Zhang ZP. Tetrahedron: Asymmetry 2006; 17: 2401
- 113 Chen Y, Yekta S, Yudin AK. Chem. Rev. 2003; 103: 3155
- 114 Aspinall HC. Chem. Rev. 2002; 102: 1807
- 115 Wang J, Li H, Yu X, Zu L, Wang W. Org. Lett. 2005; 7: 4293
- 116 McCooey SH, Connon SJ. Angew. Chem. Int. Ed. 2005; 44: 6367
- 117 Cao CL, Ye MC, Sun XL, Tang Y. Org. Lett. 2006; 8: 2901
- 118 Berkessel A, Roland K, Neudorfl JM. Org. Lett. 2006; 8: 4195
- 119 Wanka L, Cabrele C, Vanejews M, Schreiner PR. Eur. J. Org. Chem. 2007; 1474
- 120 Miyabe H, Tuchida S, Yamauchi M, Takemoto Y. Synthesis 2006; 3295
- 121 Yamoka Y, Miyabe H, Takemoto Y. J. Am. Chem. Soc. 2007; 129: 6686
- 122 Duan SW, An J, Chen JR, Xiao WJ. Org. Lett. 2011; 13: 2290
- 123 Chen WB, Wu ZJ, Hu J, Cun LF, Zhang XM, Yuan WC. Org. Lett. 2011; 13: 2472
- 124 Klauber EG, Mittal N, Shah TK, Seidel D. Org. Lett. 2011; 13: 2464
- 125 Gutiérrez-García VM, López-Ruiz H, Reyes-Rangel G, Juaristi E. Tetrahedron 2001; 57: 6487
- 126 Juaristi EE, Soloshnok VA. Enantioselective Synthesis of β-Amino Acids. John Wiley & Sons, Inc; Hoboken: 2005
- 127 Juaristi E, Quintana D, Escalante J. Aldrichimica Acta 1994; 27: 3
- 128 Cole DC. Tetrahedron 1994; 50: 9517
- 129 Seebach D, Beck AK, Bierbaum DJ. Chem. Biodivers. 2004; 1: 1111
- 130 Lelais G, Seebach D. Peptide Science 2004; 76: 206
- 131 Gmeiner P. Tetrahedron Lett. 1990; 31: 5717
- 132 Davies SG, Díez D, Sara H. Org. Biomol. Chem. 2005; 3: 1284
- 133 Myers JK, Jacobsen EN. J. Am. Chem. Soc. 1999; 121: 8959
- 134 Ting A, Schaus SE. Eur. J. Org. Chem. 2007; 5797
- 135 Alcaide B, Almendros P. Angew. Chem. Int. Ed. 2008; 47: 4632
- 136 Verkade JM. M, van Hemert LJ. C, Quaedflieg PJ. L. M, Rutjes FP. J. T. Chem. Soc. Rev. 2008; 37: 29
- 137 Wenzel AG, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 12964
- 138 Lu HH, Zhang FG, Meng XG, Duan SW, Xiao WJ. Org. Lett. 2009; 11: 3946
- 139 Poulsen TB, Alemparte C, Saaby S, Bella M, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 2896
- 140 Utsumi N, Kitagaki S, Barbas CF. Org. Lett. 2008; 10: 3405
- 141 Song J, Wang Y, Deng L. J. Am. Chem. Soc. 2006; 128: 6048
- 142 Tillman AL, Ye JX, Dixon DJ. Chem. Commun. 2006; 1191
- 143 Hegedus LS. J. Am. Chem. Soc. 2009; 131: 17995
- 144 Wenzel AG, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 12964
- 145 Wenzel AG, Lalonde MP, Jacobsen EN. Synlett 2003; 1919
- 146 Okino T, Hoashi Y, Furukawa T, Xu XN, Takemoto Y. J. Am. Chem. Soc. 2005; 127: 119
- 147 Tan C, Liu XH, Wang LW, Wang J, Feng XM. Org. Lett. 2008; 10: 5305
- 148 Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1967
- 149 Li WH, Song BA, Bhadury PS, Li L, Wang ZC, Zhang XY, Hu DY, Chen Z, Zhang YP, Bai S, Wu J, Yang S. Chirality 2012; 24: 223
- 150 Crystal data for (–)-46b: CCDC-781779; C22H23FN2O4S; Mr = 430.48; monoclinic; space group P2 (1); a = 9.1694(12) Å, b = 9.2368(11) Å, c = 13.6139(17) Å, α = 79.486(5)°, β = 72.968(5)°, γ = 79.460(5)°; V = 1073.6(2) Å3; D calc = 1.329 Mg/m3; T = 293(2) K; Z = 2; 11437 reflections collected, 3717 independent (Rint = 0.0426), final R indices [I> 2σ(I)]: R 1 = 0.0775, wR 2 = 0.1031, R indices (all data): R 1 = 0.1031, wR 2 = 0.2541, absolute structure parameter: 0.008(4), GOF = 0.974
- 151 Song J, Wang Y, Deng L. J. Am. Chem. Soc. 2006; 128: 6048
- 152 Bai S, Liang XP, Song BA, Bhadury PS, Hu DY, Yang S. Tetrahedron: Asymmetry 2011; 22: 518
- 153 Li L, Song BA, Bhadury PS, Zhang YP, Hu DY, Yang S. Eur. J. Org. Chem. 2011; 4743
- 154 Wang XF, An J, Zhang XX, Tan F, Chen JR, Xiao WJ. Org. Lett. 2011; 13: 808
- 155 Wenzel AG, Jacobsen EN. J. Am. Chem. Soc. 2002; 124: 12964
- 156 Wenzel AG, Lalonde NP, Jacobsen EN. Synlett 2003; 1919
- 157 Taylor MS, Tokunaga N, Jacobsen EN. Angew. Chem. Int. Ed. 2005; 44: 6700
- 158 Tillman AL, Ye JX, Dixon DJ. Chem. Commun. 2006; 1191
- 159 Song J, Shih HW, Deng L. Org. Lett. 2007; 9: 603