Kinetic resolution of α-substituted alkanoic acids promoted by homobenzotetramisole

Chemistry - A European Journal

Volumn 17, Issue 40, 2011, Pages 11296-11304

  Yang, Xing ^a   Birman, Vladimir B ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

acyl transfer catalysis; enantioselective esterification; homobenzotetramisole; kinetic resolution; organocatalysis

Indexed keywords

ALCOHOLYSIS; ARYLOXY; DYNAMIC KINETIC RESOLUTION; ENANTIOSELECTIVE; ENANTIOSELECTIVE ESTERIFICATION; HOMOBENZOTETRAMISOLE; KINETIC RESOLUTION; NONENZYMATIC KINETIC RESOLUTIONS; ORGANOCATALYSIS;

CATALYSIS; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; KINETICS; REACTION KINETICS;

CARBOXYLIC ACIDS;

ACID; ACID ANHYDRIDE; ALKANE; BENZOTETRAMISOLE; DRUG DERIVATIVE; TETRAMISOLE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM;

ACIDS; ALKANES; ANHYDRIDES; CATALYSIS; KINETICS; MOLECULAR STRUCTURE; STEREOISOMERISM; TETRAMISOLE;

EID: 80052338789     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101028     Document Type: Article

References (100)

1. The following reviews discuss some of the most widely used asymmetric approaches to α-substituted carboxylic acids α-functionalization of ketenes:, D. H. Paull, A. Weatherwax, T. Lectka, Tetrahedron 2009, 65, 6771
2. α-functionalization of aldehydes by enamine catalysis:, S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
3. α-alkylation by phase-transfer catalysis:, K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013
4. hydrogenation of α-substituted acrylates:, W. S. Knowles, Angew. Chem. Int. Ed. 2002, 41, 1998
5. R. Noyori, Angew. Chem. 2002, 114, 2108
6. Angew. Chem. Int. Ed. 2002, 41, 2008
7. chiral auxiliary-based approaches:, P. Arya, H. Qin, Tetrahedron 2000, 56, 917.
8. F. Faigl, E. Fogassy, M. Nõgrádi, E. Pálovics, J. Schindler, Tetrahedron: Asymmetry 2008, 19, 519.
9. H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249
10. E. Vedejs, M. Jure, Angew. Chem. 2005, 117, 4040
11. Angew. Chem. Int. Ed. 2005, 44, 3974.
12. For recent reviews, see: H. Pellissier, Tetrahedron 2008, 64, 1563
13. N. J. Turner, Curr. Opin. Chem. Biol. 2010, 14, 115
14. H. Pellissier, Adv. Synth. Catal. 2011, 353, 659.
15. J. M. J. Williams, R. J. Parker, C. Neri "Enzymatic kinetic resolution, in Enzyme Catalysis in Organic Synthesis, 2 nd ed., (Eds.: K. Drauz, H. Waldmann,), Wiley-VCH, Weinheim, 2002, pp. 287-312
16. N. J. Turner, Curr. Opin. Chem. Biol. 2004, 8, 114.
17. Nonenzymatic KR of acyl donors
18. K. Narasaka, F. Kanai, M. Okudo, N. Miyoshi, Chem. Lett. 1989, 1187
19. S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621
20. G. T. Notte, T. Sammakia, P. J. Steel, J. Am. Chem. Soc. 2005, 127, 13502
21. G. T. Notte, T. Sammakia, J. Am. Chem. Soc. 2006, 128, 4230
22. K. Ishihara, Y. Kosugi, S. Umemura, A. Sakakura, Org. Lett. 2008, 10, 3191.
23. Nonenzymatic DKR of azlactones
24. D. Seebach, G. Jaeschke, K. Gottwald, K. Matsuda, R. Formisano, D. A. Chaplin, Tetrahedron 1997, 53, 7539
25. J. Liang, J. C. Ruble, G. C. Fu, J. Org. Chem. 1998, 63, 3154
26. L. Xie, W. Hua, A. S. C. Chan, Y.-C. Leung, Tetrahedron: Asymmetry 1999, 10, 4715
27. A. Berkessel, F. Cleemann, S. Mukherjee, T. N. Müller, J. Lex, Angew. Chem. 2005, 117, 817
28. Angew. Chem. Int. Ed. 2005, 44, 807
29. A. Peschiulli, C. Quigley, S. Tallon, Yu. K. Gun'ko, S. J. Connon, J. Org. Chem. 2008, 73, 6409
30. G. Lu, V. B. Birman, Org. Lett. 2011, 13, 356.
31. Nonenzymatic DKR of other cyclic anhydrides
32. J. Hang, H. Li, L. Deng, Org. Lett. 2002, 4, 3321
33. J. Hang, L. Deng, Synlett 2003, 1927
34. L. Tang, L. Deng, J. Am. Chem. Soc. 2002, 124, 2870.
35. V. B. Birman, E. W. Uffman, H. Jiang, X. Li, C. J. Kilbane, J. Am. Chem. Soc. 2004, 126, 12226
36. V. B. Birman, H. Jiang, Org. Lett. 2005, 7, 3445
37. V. B. Birman, X. Li, Org. Lett. 2006, 8, 1351
38. V. B. Birman, X. Li, Org. Lett. 2008, 10, 1115
39. Y. Zhang, V. B. Birman, Adv. Synth. Catal. 2009, 351, 2525.
40. V. B. Birman, L. Guo, Org. Lett. 2006, 8, 4859.
41. V. B. Birman, H. Jiang, X. Li, L. Guo, E. W. Uffman, J. Am. Chem. Soc. 2006, 128, 6536.
42. V. B. Birman, H. Jiang, X. Li, Org. Lett. 2007, 9, 3237.
43. X. Li, P. Liu, K. N. Houk, V. B. Birman, J. Am. Chem. Soc. 2008, 130, 13836.
44. KR of secondary alcohols
45. I. Shiina, K. Nakata, Tetrahedron Lett. 2007, 48, 8314
46. I. Shiina, K. Nakata, K. Ono, M. Sugimoto, A. Sekiguchi, Chem. Eur. J. 2010, 16, 167
47. I. Shiina, K. Ono, K. Nakata, Chem. Lett. 2011, 40, 147
48. Q. Xu, H. Zhou, X. Geng, P. Chen, Tetrahedron 2009, 65, 2232
49. H. Zhou, Q. Xu, P. Chen, Tetrahedron 2008, 64, 6494
50. D. Belmessieri, C. Joannesse, P. A. Woods, C. MacGregor, C. Jones, C. D. Campbell, C. P. Johnston, N. Duguet, C. Concellon, R. A. Bragg, A. D. Smith, Org. Biomol. Chem. 2011, 9, 559.
51. Intramolecular ketene [2+2 cycloadditions
52. V. C. Purohit, A. S. Matla, D. Romo, J. Am. Chem. Soc. 2008, 130, 10478
53. C. A. Leverett, V. C. Purohit, D. Romo, Angew. Chem. 2010, 122, 9669
54. Angew. Chem. Int. Ed. 2010, 49, 9479
55. D. Belmessieri, L. C. Morrill, C. Simal, A. M. Z. Slawin, A. D. Smith, J. Am. Chem. Soc. 2011, 133, 2714.
56. Enantioselective Steglich rearrangement
57. F. R. Dietz, H. Gröger, Synlett 2008, 663
58. C. Joannesse, C. P. Johnston, C. Concellon, C. Simal, D. Philp, A. D. Smith, Angew. Chem. 2009, 121, 9076
59. Angew. Chem. Int. Ed. 2009, 48, 8914.
60. I. Shiina, K. Nakata, Y. Onda, Eur. J. Org. Chem. 2008, 5887.
61. For an account of our initial study, see:, X. Yang, V. B. Birman, Adv. Synth. Catal. 2009, 351, 2301.
62. Subsequently, the Shiina group found that p-methoxybenzoic anhydride can be replaced with the more effective and less expensive pivalic anhydride:, I. Shiina, K. Nakata, K. Ono, Y. Onda, M. Itagaki, J. Am. Chem. Soc. 2010, 132, 11629.
63. Recently, carbodiimide-mediated in situ generation of achiral syn-anhydrides was used in KR of trans-cyclohexane-1,2-diol:, R. Hrdina, C. E. Müller, P. R. Schreiner, Chem. Commun. 2010, 46, 2689.
64. For selected methods of preparing enantioenriched α-arylalkanoic acids and their derivatives, see: A. L. Casalnuovo, T. V. RajanBabu, T. A. Ayers, T. H. Warren, J. Am. Chem. Soc. 1994, 116, 9869
65. S. L. Wiskur, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 6176, and references therein
66. T. M. Konrad, J. A. Fuentes, A. M. Z. Slawin, M. L. Clarke, Angew. Chem. 2010, 122, 9383
67. Angew. Chem. Int. Ed. 2010, 49, 9197
68. Refs. 17, 20.
69. M. Chérest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 9, 2199
70. N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61
71. N. T. Anh, Top. Curr. Chem. 1980, 88, 145.
72. For selected methods of preparing enantioenriched α-(aryl/alkyloxy) alkanoic acids, see: D. Kato, S. Mitsuda, H. Ohta, Org. Lett. 2002, 4, 371
73. T. C. Maier, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 4594.
74. For selected methods of preparing enantioenriched α-haloalkanoic acids, see: A. G. Myers, L. McKinstry, J. K. Barbay, J. Gleason, Tetrahedron Lett. 1998, 39, 1335
75. D. H. Paull, M. T. Scerba, E. Alden-Danforth, L. R. Widger, T. Lectka, J. Am. Chem. Soc. 2008, 130, 17260
76. S. France, H. Wack, A. E. Taggi, A. M. Hafez, T. R. Wagerle, M. H. Shah, C. L. Dusich, T. Lectka, J. Am. Chem. Soc. 2004, 126, 4245
77. M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108
78. N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790.
79. Asymmetric Synthesis and Application of α-Amino Acids (Eds., V. A. Soloshonok, K. Izawa,), ACS, New York, 2009, p. 1009
80. J.-A. Ma, Angew. Chem. 2003, 115, 4426
81. Angew. Chem. Int. Ed. 2003, 42, 4290
82. R. M. Williams, Synthesis of Optically Active R-Amino Acids, Pergamon, Oxford, 1989.
83. For selected methods of preparing enantioenriched α-azidoalkanoic acids, see: D. A. Evans, T. C. Britton, J. A. Ellman, R. L. Dorow, J. Am. Chem. Soc. 1990, 112, 4011
84. E. J. Corey, J. O. Link, J. Am. Chem. Soc. 1992, 114, 1906
85. C. W. Tornøe, T. Sonke, I. Maes, H. E. Schoemaker, M. Meldal, Tetrahedron: Asymmetry 2000, 11, 1239.
86. For selected methods of preparing enantioenriched α-amino acids and their derivatives, see: U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793
87. Angew. Chem. Int. Ed. Engl. 1981, 20, 798
88. M. S. Sigman, P. Vachal, E. N. Jacobsen, Angew. Chem. 2000, 112, 1336
89. Angew. Chem. Int. Ed. 2000, 39, 1279
90. E. C. Lee, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 12066.
91. For selected methods of preparing enantioenriched α- phthalimidoalkanoic acids, see: M. Calmes, C. Glot, T. Michel, M. Rolland, J. Martinez, Tetrahedron: Asymmetry 2000, 11, 737
92. J. Chen, Q. Liu, A. Lei, X. Zhang, W. Zhang, S. Spinella, Org. Lett. 2008, 10, 3033.
93. X. Yang, G. Lu, V. B. Birman, Org. Lett. 2010, 12, 892.
94. For selected methods of preparing enantioenriched α-(arylthio) alkanoic acids, see: T. Yura, N. Iwasawa, R. Clark, T. Mukaiyama, Chem. Lett. 1986, 1809
95. D. S. Tan, M. M. Günter, D. G. Drueckhammer, J. Am. Chem. Soc. 1995, 117, 9093
96. P.-J. Um, D. G. Drueckhammer, J. Am. Chem. Soc. 1998, 120, 5605.
97. For a preliminary account of this study, see:, X. Yang, V. B. Birman, Angew. Chem. 2011, 123, 5667
98. Angew. Chem. Int. Ed. 2011, 50, 5553.
99. M. Kobayashi, S. Okamoto, Tetrahedron Lett. 2006, 47, 4347
100. V. B. Birman, X. Li, Z. Han, Org. Lett. 2007, 9, 37.