Asymmetric induction by (S)-4-isopropyl-1-phenylimidazolidin-2-thione in titanium-mediated aldol reactions and its application in enantioselective synthesis of (R)-baclofen

Synthesis

Volumn , Issue 19, 2011, Pages 3123-3132

  Khatik, Gopal L ^a   Khurana, Ravi ^a   Kumar, Varun ^a   Nair, Vipin A ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

aldol reaction; asymmetric synthesis; chiral auxiliaries; stereoselectivity; titanium

Indexed keywords

ALDOL REACTIONS; ASYMMETRIC INDUCTION; ASYMMETRIC SYNTHESIS; BACLOFEN; CHIRAL AUXILIARIES; ENANTIOSELECTIVE SYNTHESIS; STEREO-SELECTIVE;

CONDENSATION REACTIONS; ENANTIOSELECTIVITY; STEREOSELECTIVITY; TITANIUM; VOLATILE FATTY ACIDS;

SYNTHESIS (CHEMICAL);

1 PHENYLPROPANE 1,3 DIOL; 2 METHYL 1 PHENYLPROPANE 1,3 DIOL; 3 (4 BROMOPHENYL) 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 3 (4 METHOXYPHENYL) 2 METHYLPROPAN 1 ONE; 3 (4 BROMOPHENYL) 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL]PROPAN 1 ONE; 3 (4 CHLOROPHENYL) 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL]PROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 2 METHYL 3 4 TOLYLPROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 2 METHYL 3 PHENYLPROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 2 METHYL 5 PHENYLPENT 4 EN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 2 METHYLPENTAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 2,4 DIMETHYLPENTAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 3 (4 METHOXYPHENYL) 2 METHYLPROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 3 (4 METHOXYPHENYL)PROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 3 4 TOLYLPROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 3 PHENYLPROPAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 4,4 DIMETHYLPENTAN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 5 METHYLHEX 4 EN 1 ONE; 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 5 PHENYLPENT 4 EN 1 ONE; 3 HYDROXY 2 METHYL 3 PHENYLPROPANOIC ACID; 3 PHENYLHYDRACRYLIC ACID; 4 (4 CHLOROPHENYL) 3 HYDROXY 1 [5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 1 YL] 3 (4 METHOXYPHENYL) 2 METHYLPROPAN 1 ONE; 4 ISOPROPYL 1 PHENYLIMIDAZOLIDIN 2 THIONE; 5 ISOPROPYL 3 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; ALDEHYDE; BACLOFEN; BENZALDEHYDE; IMIDAZOLIDINE DERIVATIVE; N ACETYL 4 ISOPROPYL 1 PHENYLIMIDAZOLIDIN 2 THIONE; N PROPIONYL 4 ISOPROPYL 1 PHENYLIMIDAZOLIDIN 2 THIONE; TITANIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALDOL REACTION; ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHELATION; CHIRALITY; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH RESOLUTION MELTING ANALYSIS; HYDROLYSIS; MELTING POINT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 80053053421     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260187     Document Type: Article

References (75)

1. Kleschick W A., Buse C T., Heathcock C H., J. Am. Chem. Soc. 1977 99 247
2. Buse C T., Heathcock C H., J. Am. Chem. Soc. 1977 99 8109
3. Evans D A., Vogel E, Nelson J V., J. Am. Chem. Soc. 1979 101 6120
4. Masamune S, Choy W, Francis A J. K., Imperiali B, J. Am. Chem. Soc. 1981 103 1566
5. Evans D A., Bartroli J, Shih T L., J. Am. Chem. Soc. 1981 103 2127
6. Evans D A., Rieger D L., Bilodeau M T., Urpi F, [nl]J. Am. Chem. Soc. 1991 113 1047
7. Reetz M T., Peter R, Tetrahedron Lett. 1981 22 4691
8. Siegel C, Thornton E R., J. Am. Chem. Soc. 1989 111 5722
9. Walker M A., Heathcock C H., J. Org. Chem. 1991 56 5747
10. Nagao Y, Hagiwara Y, Kumagai T, Ochiai M, Inoue T, Hashimoto K, Fujita E, J. Org. Chem. 1986 51 2391
11. Nagao Y, Yamada S, Kumagai T, Ochiai M, Fujita E, J. Chem. Soc., Chem. Commun. 1985 1418
12. Bonner M P., Thornton E R., J. Am. Chem. Soc. 1991 113 1299
13. Crimmins M T., King B W., Tabet E A., J. Am. Chem. Soc. 1997 119 7883
14. Nerz-Stormes M, Thornton E R., J. Org. Chem. 1991 56 2489
15. Crimmins M T., Chaudhary K, Org. Lett. 2000 2 775
16. Hodge M B., Olivo H F., Tetrahedron 2004 60 9397
17. Cosp A, Romea P, Urpi F, Vilarrasa J, Tetrahedron Lett. 2001 42 4629
18. Crimmins M T., King B W., Tabet E A., Chaudhary K, J. Org. Chem. 2001 66 894
19. Kim T H., Lee G.-J, Tetrahedron Lett. 2000 41 1505
20. Chun C C., Lee G.-J, Kim J N., Kim T H., Tetrahedron: Asymmetry 2005 16 2989
21. AbdelAziz A A.-M, Okuno J, Tanaka S, Ishizuka T, Matsunaga H, Kunieda T, Tetrahedron Lett. 2000 41 8533
22. Roos G H. P., Balasubramaniam S, Tetrahedron: Asymmetry 1998 9 923
23. Königsberger K, Prasad K, Repic O, Blacklock T J., Tetrahedron: Asymmetry 1997 8 2347
24. Guz N R., Phillips A J., Org. Lett. 2002 4 2253
25. Zhang Y, Phillips A J., Sammakia T, Org. Lett. 2004 6 23
26. Zhang Y, Sammakia T, Org. Lett. 2004 6 3139
27. Crimmins M T., Shamszad M, Org. Lett. 2011 9 149; and reference cited therein
28. Evans D A., Tedrow J S., Shaw J T., Downey C W., [nl] J. Am. Chem. Soc. 2002 124 392
29. Shinisha C B., Sunoj R B., J. Am. Chem. Soc. 2010 132 12319
30. Gnas Y, Glorius F, Synthesis 2006 1899; and references cited therein
31. Geary L M., Hultin P G., Tetrahedron: Asymmetry 2009 20 131; and references cited therein
32. Brodmann T, Lorenz R, Schackel R, Simsek S, Kalesse M, Synlett 2009 174
33. Li J, Menche D, Synthesis 2009 2293
34. Czekelius C, Tzschucke C C., Synthesis 2010 543
35. Rinner U, Lentsch C, Aichinger C, Synthesis 2010 3763
36. Kotha S, Deb A C., Lahiri K, Manivannan E, Synthesis 2009 165
37. Khatik G L., Pal A, Apsunde T D., Nair V A., [nl]J. Heterocycl. Chem. 2010 47 734
38. Kumar V, Nair V A., Tetrahedron Lett. 2010 51 966
39. Kumar V, Raghavaiah P, Mobin S M., Nair V A., Org. Biomol. Chem. 2010 8 4960
40. Sharma R, Chouhan M, Nair V A., Tetrahedron Lett. 2010 51 2039
41. Khatik G L., Pal A, Mobin S M., Nair V A., Tetrahedron Lett. 2010 51 3654
42. Khatik G L., Kaur J, Kumar V, Venugopalan P, Tikoo K, Nair V A., Eur. J. Med. Chem. 2011 46 3291
43. Ganesan A, Pure Appl. Chem. 2001 73 1033
44. For H NMR vicinal coupling constants, see:, Kleschick W A., Buse C T., Heathcock C H., J. Am. Chem. Soc. 1977 99 247
45. Oppolzer W, Blagg J, Rodriguez I, Walther E, J. Am. Chem. Soc. 1990 112 2767
46. Nebot J, Figueras S, Romea P, Urpi F, Ji Y, Tetrahedron 2006 62 11090
47. Yan T H., Hung H C., Hung A W., Lee H C., Chang C S., J. Org. Chem. 1994 59 8187
48. Glorius F, Spielkamp N, Holle S, Goddard R, Lehmann C W., Angew. Chem. Int. Ed. 2004 43 2850
49. Glorius F, Org. Biomol. Chem. 2005 3 4171
50. Evans D A., Nelson J V., Vogel E, Taber T R., J. Am. Chem. Soc. 1981 103 3099
51. Olpe H R., Demiville H, Baltzer V, Bencze W L., Koella W P., Wolf P, Haas H L., Eur. J. Pharmacol. 1978 52 133
52. Camps P, Munoz-Torrero D, Sanchez L, Tetrahedron: Asymmetry 2004 15 2039
53. Chnevert R, Desjardins M, Tetrahedron Lett. 1991 32 4249
54. Felluga F, Gombac V, Pitacco G, Valentin E, Tetrahedron: Asymmetry 2005 16 1341
55. Wang M.-X, Zhao S.-M, Tetrahedron Lett. 2002 43 6617
56. Herdeis C, Hubmann H P., Tetrahedron: Asymmetry 1992 3 1213
57. Chenevert R, Desjardins M, Can. J. Chem. 1994 72 2312
58. Yoshifuji S, Kaname M, Chem. Pharm. Bull. 1995 43 1302
59. Langlois N, Dahuron N, Wang H S., Tetrahedron 1996 48 15117
60. Thakur V V., Paraskar A S., Sudalai A, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2007 46 326
61. Corey E J., Zhang F.-Y, Org. Lett. 2000 2 4257
62. Gotoh H, Ishikawa H, Hayashi Y, Org. Lett. 2007 9 5307
63. Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y, J. Am. Chem. Soc. 2005 127 119
64. Wang Y, Li P, Liang X, Zhang T Y., Ye J, Chem. Commun. 2008 1232
65. Garca-Garca P, Ladpche A, Halder R, List B, Angew. Chem. Int. Ed. 2008 47 4719
66. Zu L, Xie H, Li H, Wang J, Wang W, Adv. Synth. Catal. 2007 349 2521
67. Thakur V V., Nikalje M D., Sudalai A, Tetrahedron: Asymmetry 2003 14 581
68. Resende P, Almeida W P., Coelho F, Tetrahedron: Asymmetry 1999 10 2113
69. Brenna E, Caraccia N, Fuganti C, Fuganti D, Grasselli P, Tetrahedron: Asymmetry 1997 8 3801
70. Nemoto T, Jin L, Nakamura H, Hamada Y, Tetrahedron Lett. 2007 47 6577
71. Baldoli C, Maiorana S, Licandro E, Perdicchia D, Vandoni B, Tetrahedron: Asymmetry 2000 11 2007
72. Shao C, Yu H.-J, Wu N.-Y, Tian P, Wang R, Feng C.-G, Lin [nl]G.-Q, Org. Lett. 2011 13 788
73. Schoenfelder A, Mann A, LeCoz S, Synlett 1993 63
74. Armstrong A, Convine N J., Popkin M E., Synlett 2006 1589
75. Soli E D., Manoso A S., Patterson M C., DeShong P, [nl]J. Org. Chem. 1999 64 3171