Asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid using a 1,2-addition of PhMgBr to an N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA

Tetrahedron Asymmetry

Volumn 21, Issue 21-22, 2010, Pages 2619-2624

  Babu, K Chandra ^a,b   Vysabhattar, Raman ^a   Srinivas, K S V ^a   Nigam, Satish ^a   Madhusudhan, G ^a   Mukkanti, K ^b  

^a GVK BIOSCIENCES PVT LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXO 4 PHENYLOXAZOLIDINE 5 CARBOXYLIC ACID; 2,2 DIMETHYL 1,3 DIOXOLAN 4 YL METHANOL; 2,2 DIMETHYL 1,3 DIOXOLAN 4 YL) METHYL BENZOATE; 2,2 DIMETHYL 1,3 DIOXOLANE 4 CARBALDEHYDE; 3 AMINO 3 PHENYLPROPANE 1,2 DIOL HYDROCHLORIDE; 4 CHLOROMETHYL 2,2 DIMETHYL 1,3 DIOXOLANE; 5 (HYDROXYL METHYL) 4 PHENYLOXAZOLIDIN 2 ONE; 5 (HYDROXYMETHYL) 4 PHENYLOXAZOLIDIN 2 ONE; AMIDE; CARBOXYLIC ACID; EPICHLOROHYDRIN; GLYCERALDEHYDE; N (2,2 DIMETHYL 1,3 DIOXOLAN 4 YL)(PHENYL)METHYL 2 METHYL PROPANE 2 SULFINAMIDE; N (2,2 DIMETHYL 1,3 DIOXOLAN 4 YL)METHYLENE 2 METHYLPROPANE 2 SULFINAMIDE; TERT BUTYL 2,3 DIHYDROXY 1 PHENYLPROPYLCARBAMATE; TERT BUTYLSULFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; GRIGNARD REACTION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 78649893956     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.10.012     Document Type: Article

References (62)

1. M. Past, A. Moyano, M.A. Perichs, and A. Riera Tetrahedron: Asymmetry 7 1996 243 262
2. H. Kakeya, M. Morishita, K. Kobinata, M. Osono, M. Ishizuka, and H. Osada J. Antibiot. 51 1998 1126 1128
3. H. Kakeya, M. Morishita, H. Koshino, T. Morita, K. Kobayashi, and H. Osada J. Org. Chem. 64 1999 1052 1053
4. A. Grajewska, and M.D. Rozwado wska Tetrahedron: Asymmetry 18 2007 803 813
5. C.H. Senanayake Aldrichim. Acta 31 1998 3 15
6. I. Gallou, and C.H. Senanayake Chem. Rev. 106 2006 2843 2874
7. E.J. Kim, K.M. An, and S.Y. Ko Bull. Korean Chem. Soc. 27 2006 2019 2022
8. V. Ferran, A. Moyano, M.A. Pericas, and A. Riera J. Org. Chem. 62 1997 4970 4982
9. C. Puigjaner, V.A. Ferran, A. Moyano, M.A. Pericas, and A. Riera J. Org. Chem. 64 1999 7902 7911
10. T. Matsui, T. Kondo, Y. Nishita, S. Itadani, H. Tsuruta, S. Fujita, N. Omawari, M. Sakai, S. Nakazawa, A. Ogata, H. Mori, W. Kamoshima, K. Terai, H. Ohno, T. Obata, H. Nakai, and M. Todab Bioorg. Med. Chem. 10 2002 3787 3805
11. M. Poch, M. Alcon, A. Moyano, M. Pen, and A. Riera Tetrahedron Lett. 34 1993 7781 7784
12. H.T. Chang, and K.B. Sharpless Tetrahedron Lett. 37 1996 3219 3222
13. Y. Sakamoto, A. Shiraishi, J. Seonhee, and T. Nakata Tetrahedron Lett. 40 1999 4203 4206
14. S. Milicevic, R. Matovic, and R.N. Saicica Tetrahedron Lett. 45 2004 955 957
15. S.G. Davies, D.G. Hughes, R.L. Nicholson, A.D. Smith, and A.J. Wright Org. Biomol. Chem. 2 2004 1549 1553
16. A.S. Paraskar, and A. Sudalai Tetrahedron 62 2006 5756 5762
17. S. George, S.V. Narina, and A. Sudalai Tetrahedron Lett. 48 2007 1375 1378
18. M.E. Bunnage, A.N. Chernega, S.G. Davies, and C.J. Goodwin J. Chem. Soc., Perkin Trans. 1 1994 2373 2384
19. M.E. Bunnage, S.G. Davies, and C.J. Goodwin Synlett 1993 731 732
20. M.E. Bunnage, S.G. Davies, C.J. Goodwin, and O. Ichihara Tetrahedron 50 1994 3975 3986
21. G. Bashiardes, G.J. Bodwell, and S.G. Davies J. Chem. Soc., Perkin Trans. 1 1993 459 469
22. M.E. Bunnage, S.G. Davies, and C.J. Goodwin J. Chem. Soc., Perkin Trans. 1 1994 2385 2391
23. G. Madhusudhan, G.O. Reddy, J. Ramanatham, and P.K. Dubey Tetrahedron Lett. 44 2003 6323 6325
24. D.A. Cogan, G. Liu, and J. Ellman Tetrahedron 55 1999 8883 8904
25. N.R. Swamy, P. Krishnaiah, N. Srinivasa Reddy, and Y.J. Venkates-warlu Carbohydr. Chem. 23 2004 217 222
26. Y.-L. Wu, W.-L. Wu, Y.-L. Li, X.-L. Sun, and Z.-H. Peng Pure Appl. Chem. 68 1996 727 734
27. J.A. Marshall, and G.P. Luke J. Org. Chem. 58 1993 6229 6234
28. H. Arasaki, M. Iwata, M. Makida, and Y. Masaki Chem. Pharm. Bull. 52 2004 848 852
29. H. Matsunaga, T. Sakamaki, H. Nagaoka, and Y. Yamada Tetrahedron Lett. 24 1983 3009 3012
30. S.-K. Kang, and D.-S. Shin Bull. Korean Chem. Soc. 8 1987 215 216
31. N. Minami, S.S. Ko, and Y. Kishi J. Am. Chem. Soc. 104 1982 1109 1111
32. D.R. Wagle, C. Garai, J. Chiang, M.G. Monteleone, B.E. Kurys, T.W. Strohmeyer, V.R. Hegde, M.S. Manhas, and A.K. Bose J. Org. Chem. 53 1988 4227 4236
33. M. Kusakabe, and F. Sato Chem. Lett. 1986 1473 1476
34. G.Y. Xu, Y. Zhou, and M.C. Xu Chin. Chem. Lett. 17 2006 302 304
35. E. Baer, and H.O.L. Fisher J. Biol. Chem. 128 1939 463 473
36. G.J.F. Chittenden Carbohydr. Res. 84 1980 350 352
37. J.L. Debost, J. Gelas, and D. Horton J. Org. Chem. 48 1983 1381 1382
38. J. Kuszmann, E. Tomori, and I. Meerwald Carbohydr. Res. 128 1984 87 99
39. G. Kohan, and G. Just Synthesis 1974 192
40. C. Morpain, B. Nasser, B. Laude, and N. Latruffe Org. Prep. Proced. Int. 22 1990 540 543
41. R.S. Tipson, and A. Cohen Carbohydr. Res. 7 1968 232 243
42. R.W. Kierstead, A. Faraone, F. Mennona, J. Mullin, R.W. Guthrie, H. Crowley, B. Simko, and L.C. Blaber J. Med. Chem. 26 1983 1561 1569
43. B.T. Golding, and P.V. Ioannou Synthesis 1977 423 424
44. J.J. Baldwin, A.W. Raab, K. Mensler, B.H. Arison, and D.E. McClure J. Org. Chem. 43 1978 4876 4878
45. G. Hirth, and W. Walther Helv. Chim. Acta 68 1985 1863 1871
46. S. Takano, A. Kurotaki, M. Takahashi, and K. Ogasawara Synthesis 1986 403 406
47. H. Christian Synthesis 11 1986 962 964
48. C. Hubschwerlen, J.L. Specklin, and J. Higelin Org. Synth. 72 1993 1
49. M.E. Jung, and T.J. Shaw J. Am. Chem. Soc. 102 1980 6304 6311
50. E. Abushnab, P. Venishetti, R.W. Leiby, H.K. Singh, A.B. Mikkilineni, R. Saibaba, and P. Panzica J. Org. Chem. 53 1988 2598 2602
51. P. Camps, and X. Farres Tetrahedron: Asymmetry 6 1995 1283 1294
52. D.R.J. Kodali Lipid Res. 28 1987 464 469
53. R. Azzouz, C. Fruit, L. Bischoff, and F. Marsais J. Org. Chem. 73 2008 1154 1157
54. A.K.L. Provins, and A. Froidbise Tetrahedron Lett. 39 1998 1437 1440
55. K. Chandra Babu, G. Ramadasu, L. Gangaiah, G. Madhusudhan, and K. Mukkanti Indian J. Chem. 49B 2010 260 263
56. D.L. Enders, and U. Reinhold Tetrahedron: Asymmetry 8 1997 1895 1946
57. D. Morton, and R.A. Stockman Tetrahedron 62 2006 8869 8905
58. R. Badorrey, C. Cativiela, D. Maria, D. Villegas, and J. Gdlvez Tetrahedron 53 1999 1411 1416
59. J.W. Evans, and J. Ellman J. Org. Chem. 68 2003 9948 9957
60. A. Madhan, A.R. Kumar, and B.V. Rao Tetrahedron: Asymmetry 12 2001 2009 2011
61. H. Hiinig, P.S. Wasserthal, and H. Weber Tetrahedron 46 1990 3841 3850
62. D. Lee, K.C. Kim, and M.J. Kim Tetrahedron Lett. 39 1998 9039 9042