Organocatalytic asymmetric hydrophosphonylation/Mannich reactions using thiourea, cinchona and brnsted acid catalysts

Synlett

Volumn 23, Issue 8, 2012, Pages 1108-1131

  Bhadury, Pinaki S ^a   Li, Hu ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

absolute configuration; Brnsted acids; chirality; diastereoselectivity; enantioselectivity; organocatalysts

Indexed keywords

ALPHA AMINOPHOSPHONATE DERIVATIVE; BENZOTHIAZOLE; BRONSTED ACID; CINCHONA ALKALOID; CINNAMALDEHYDE; DICHLOROMETHANE; PHOSPHONIC ACID DERIVATIVE; TETRAHYDROFURAN; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CAPILLARY ELECTROPHORESIS; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; DIELS ALDER REACTION; ELECTROPHILICITY; ENANTIOMER; ETHERIFICATION; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROGENATION; HYDROPHOSPHONYLATION; KABACHNIK FIELDS REACTION; MANNICH REACTION; MICHAEL ADDITION; NUCLEOPHILICITY; PHARMACOPHORE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROCESS OPTIMIZATION; STEREOCHEMISTRY; SUZUKI REACTION; X RAY DIFFRACTION;

EID: 84860635792     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290193     Document Type: Article

References (158)

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. Ordez 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, Jrgensen 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, Rudziska E, Mucha A, Kafarski P. Tetrahedron: Asymmetry: 2004; 15 1597
87. Berlicki L, Rudziska E, Kafarski P. Tetrahedron: Asymmetry: 2003; 14 1535
88. Okamoto Y, Kaida Y. J. Chromatogr., A: 1994; 666 403
89. Lmmerhofer 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. Rudziska 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. Gutirrez-Garca VM, Lpez-Ruiz H, Reyes-Rangel G, Juaristi E. Tetrahedron: 2001; 57 6487
126. Juaristi EE, Soloshnok VA. Enantioselective Synthesis of -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, Dez 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, Jrgensen 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, Csmpai A, Sos 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. Song J, Wang Y, Deng L. J. Am. Chem. Soc.: 2006; 128 6048
151. Bai S, Liang XP, Song BA, Bhadury PS, Hu DY, Yang S. Tetrahedron: Asymmetry: 2011; 22 518
152. Li L, Song BA, Bhadury PS, Zhang YP, Hu DY, Yang S. Eur. J. Org. Chem.: 2011; 4743
153. Wang XF, An J, Zhang XX, Tan F, Chen JR, Xiao WJ. Org. Lett.: 2011; 13 808
154. Wenzel AG, Jacobsen EN. J. Am. Chem. Soc.: 2002; 124 12964
155. Wenzel AG, Lalonde NP, Jacobsen EN. Synlett: 2003; 1919
156. Taylor MS, Tokunaga N, Jacobsen EN. Angew. Chem. Int. Ed.: 2005; 44 6700
157. Tillman AL, Ye JX, Dixon DJ. Chem. Commun.: 2006; 1191
158. Song J, Shih HW, Deng L. Org. Lett.: 2007; 9 603