SCOPUS 정보 검색 플랫폼

Volumn 2, Issue 8, 2005, Pages 721-724

The use of enantiomerically pure α,β-unsaturated N-acyloxazolidin-2-one in diastereoselective Baylis-Hillman type reaction mediated by SmI2

(5) Mamaghani, Manouchehr a Yazdanbakhsh, Mohammad Reza a Badrian, Abed b Valizadeh, Hassan c Samimi, Heshmat Allah a

a UNIVERSITY OF GUILAN (Iran)

b Research Institution for Curriculum Development and Educational Innovations (Iran)

c AZARBAIJAN SHAHID MADANI UNIVERSITY (Iran)

Author keywords

, unsaturated N acyloxazolidin 2 one; Auxiliary; Baylis Hillman; Diastereoselective; Samarium diiodide

Indexed keywords

EID: 46149105957 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017805774717607 Document Type: Review

Times cited : (10)

References (57)

1
- 0034283585
- Langer, P. Angew. Chem. Int. Ed.2000,39, 3049;
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3049
- Langer, P.¹

2
- 0000892247
- (b) Ciganek, E. Org. React. 1997, 51, 201;
- (1997) Org. React , vol.51 , pp. 201
- Ciganek, E.¹

3
- 46149114080
- Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988,44, 4653. (d) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996,52, 8001.
- (c) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988,44, 4653. (d) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996,52, 8001.

4
- 0035817129
- (a) Mateus, C. R., Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, N.-P. Tetrahedron 2001, 57, 6901;
- (2001) Tetrahedron , vol.57 , pp. 6901
- Mateus, C.R.¹ Feltrin, M.P.² Costa, A.M.³ Coelho, F.⁴ Almeida, N.-P.⁵

5
- 0035968965
- (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867;
- (2001) Tetrahedron Lett , vol.42 , pp. 7867
- Iwabuchi, Y.¹ Sugihara, T.² Esumi, T.³ Hatakeyama, S.⁴

6
- 0035823715
- (c) Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030;
- (2001) Chem. Commun , pp. 2030
- Iwabuchi, Y.¹ Furukawa, M.² Esumi, T.³ Hatakeyama, S.⁴

7
- 0035185234
- (d) Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85;
- (2001) Tetrahedron Lett , vol.42 , pp. 85
- Basavaiah, D.¹ Kumaragurubaran, N.² Sharada, D.S.³

8
- 0033522942
- (e) Paquette, L.A.; Andino, J.M. Tetrahedron Lett. 1999, 40, 4301;
- (1999) Tetrahedron Lett , vol.40 , pp. 4301
- Paquette, L.A.¹ Andino, J.M.²

9
- 0028284153
- (f) Basavaiah, D.; Pandiaraju, S.; Sarma, P. K. S. Tetrahedron Lett. 1994, 35, 4227;
- (1994) Tetrahedron Lett , vol.35 , pp. 4227
- Basavaiah, D.¹ Pandiaraju, S.² Sarma, P.K.S.³

10
- 0025863805
- (g) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213;
- (1991) Helv. Chim. Acta , vol.74 , pp. 1213
- Buchholz, R.¹ Hoffmann, H.M.R.²

11
- 37049072798
- (h) Weichert, A.; Hoffmann, H. M. R. J Chem. Soc., Perkin Trans. 1 1990, 2154.
- (1990) J Chem. Soc., Perkin Trans. 1 , pp. 2154
- Weichert, A.¹ Hoffmann, H.M.R.²

12
- 0024832316
- A mri, H.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1989 30, 7381.
- (i) A mri, H.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1989 30, 7381.

13
- 0037169021
- and references cited therein;
- (a) Aggarawal, V. K.; Dean, D. K.; Mereu, A. and Williams, R. J. Org. Chem. 2002,67, 510 and references cited therein;
- (2002) J. Org. Chem , vol.67 , pp. 510
- Aggarawal, V.K.¹ Dean, D.K.² Mereu, A.³ Williams, R.⁴

14
- 0000737917
- (b) Hill, J. S.; Isaacs, N. S. Tetrahedron Lett. 1986, 27, 5007;
- (1986) Tetrahedron Lett , vol.27 , pp. 5007
- Hill, J.S.¹ Isaacs, N.S.²

15
- 46149111611
- (c) Hill, J. S. and Isaacs, N. S. J. Chem. Res. 1998, 330.
- (1998) J. Chem. Res , pp. 330
- Hill, J.S.¹ Isaacs, N.S.²

16
- 46149093623
- For refewces prior to 1906 see Ref Id;
- For refewces prior to 1906 see Ref Id;

17
- 0037423177
- (a) Yang, K.-S.; Lee, W.-D; Pan, J.-F.; Chen, K. J. Org. Chem. 2003, 68, 915;
- (2003) J. Org. Chem , vol.68 , pp. 915
- Yang, K.-S.¹ Lee, W.-D.² Pan, J.-F.³ Chen, K.⁴

18
- 0037127529
- (b) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedton Lett. 2002, 43, 1577;
- (2002) Tetrahedton Lett , vol.43 , pp. 1577
- Aggarwal, V.K.¹ Castro, A.M.M.² Mereu, A.³ Adams, H.⁴

19
- 0031004738
- (c) Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 4317
- Brzezinski, L.J.¹ Rafel, S.² Leahy, J.W.³

20
- 0001809397
- (a) Oppolzer, W. Pure and Appl. Chem. 1998, 60, 39;
- (1998) Pure and Appl. Chem , vol.60 , pp. 39
- Oppolzer, W.¹

21
- 3242891989
- (b) Davies, S. G. Aldrichimica Acta 1990, 23, 39;
- (1990) Aldrichimica Acta , vol.23 , pp. 39
- Davies, S.G.¹

22
- 84980162973
- (c) Enders D. and Eichenauer H. Angew. Chem., Int. Ed. Engl. 1976, 15, 549;
- (1976) Angew. Chem., Int. Ed. Engl , vol.15 , pp. 549
- Enders, D.¹ Eichenauer, H.²

23
- 33847803617
- (d) Meyers, A. I.; Knaus G.; Kamata, K. J. Am. Chem. Soc. 1974, 96, 268.
- (1974) J. Am. Chem. Soc , vol.96 , pp. 268
- Meyers, A.I.¹ Knaus, G.² Kamata, K.³

24
- 0002165370
- Evans, D. A. Aldrichimica Acta 1982, 15, 23.
- (1982) Aldrichimica Acta , vol.15 , pp. 23
- Evans, D.A.¹

25
- 0028901621
- (a) Davies, S. G.; Sanganee, H. J. Tetrahedron: Asymmetry 1995, 6, 671;
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 671
- Davies, S.G.¹ Sanganee, H.J.²

26
- 0028330352
- (b) Davies, S. G.; Doisneau, G. J. M.; Prodger, J. C.; Sanganee, H. J. Tetrahedron Lett. 1994, 35, 2369;
- (1994) Tetrahedron Lett , vol.35 , pp. 2369
- Davies, S.G.¹ Doisneau, G.J.M.² Prodger, J.C.³ Sanganee, H.J.⁴

27
- 0028355067
- (c) Davies, S. G.; Doisneau, G. J. M., Prodger, J. C.; Sanganee, H. J. Tetrahedron Lett. 1994, 35, 2373.
- (1994) Tetrahedron Lett , vol.35 , pp. 2373
- Davies, S.G.¹ Doisneau, G.J.M.² Prodger, J.C.³ Sanganee, H.J.⁴

28
- 0001260024
- Yang, K.-S.; Chen K. Org. Lett. 2000, 2, 729.
- (2000) Org. Lett , vol.2 , pp. 729
- Yang, K.-S.¹ Chen, K.²

29
- 46149104905
- (a) Youn; S. W.; Park, H. S.; Kim, Y. H. Chem. Commun. 2000, 2005;
- (2005) Chem. Commun , vol.2000
- Youn, S.W.¹ Park, H.S.² Kim, Y.H.³

30
- 0032537215
- (b) Du, X. H.; Armstrong, R. W. Tetrahedron Lett. 1998, 39, 2281.
- (1998) Tetrahedron Lett , vol.39 , pp. 2281
- Du, X.H.¹ Armstrong, R.W.²

31
- 1642538412
- (a) Mamaghani, M.; Badrian, A. Tetrahedron Lett. 2004, 45, 1547-1550;
- (2004) Tetrahedron Lett , vol.45 , pp. 1547-1550
- Mamaghani, M.¹ Badrian, A.²

32
- 3042825526
- (b) Mamaghani, M.; Badrian, A. Phosphorus, Sulfur, and Silicon 2004, 179, 1181;
- (2004) Phosphorus, Sulfur, and Silicon , vol.179 , pp. 1181
- Mamaghani, M.¹ Badrian, A.²

33
- 3242887616
- (c) Mamaghani, M. Tabatabaeian K.; Badrian, A. Phosphorus, Sulfur, and Silicon 2004, 179, 1347.
- (2004) Phosphorus, Sulfur, and Silicon , vol.179 , pp. 1347
- Mamaghani, M.¹ Tabatabaeian, K.² Badrian, A.³

34
- 0033104486
- P
- (a) Davies, S. G.; Sanganee, H. J. and Szolcsanyi, P. Tetrahedron 1999, 55 P 3337;
- (1999) Tetrahedron , vol.55 , pp. 3337
- Davies, S.G.¹ Sanganee, H.J.² Szolcsanyi, P.³

35
- 0001327462
- (b) Bull S. D.; Davies, S. G.; Jones, S.; Polywka, M. E. C.; Prasad, R. S.; Sanganee, H. J. Synlett 1998, 519.
- (1998) Synlett , pp. 519
- Bull, S.D.¹ Davies, S.G.² Jones, S.³ Polywka, M.E.C.⁴ Prasad, R.S.⁵ Sanganee, H.J.⁶

36
- 0023802574
- (a) Ploux, O.; Caruso, M.; Chassaing, G.; Marquet, A. J. Org. Chem. 1988, 53, 3154
- (1988) J. Org. Chem , vol.53 , pp. 3154
- Ploux, O.¹ Caruso, M.² Chassaing, G.³ Marquet, A.⁴

37
- 0028215142
- (b) Garnet, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 1994, 35, 1653.
- (1994) Tetrahedron Lett , vol.35 , pp. 1653
- Garnet, P.¹ Dogan, O.² Pillai, S.³

38
- 46149086050
- Preparation of (R)-3-(2-Bromo-3-phenyl-acryloyl, 5,5-dimethyl-4-phenyl-oxazolidin-2-one 3. To a solution of 2 (6.42 g, 20.0 mmol) in CHCl3 (60 mL) was added dropwise of Br2 (1.5 mL, 26 mmol) dissolved in CHCl3 (15 mL, The resulting mixture was stirred at room temperature and rapidly (3 h) discolorated. After evaporation of the solvent and unreacted Br2 in vacuo, the oily residue was dissolved again in CHCl3 (50 mL, To this solution was added dropwise of Et3N (5 g, 2.5 mol eq) and the resulting reaction mixture was stirred (3 h) till completion (judged by TLC, The cooled reaction mixture was diluted with CHCl3 and washed successively with 0.1 N HCl, sat. NaHCO3sol n, brine, and dried (MgSO4, Evaporation of the solvent gave the crude product. The product was recrystallized from petroleum ether/ethyl acetate 3:2 to give the title compound 3 (6.86 g, 17.2 mmol) as a
- 3): δ,1.04 (s, 3H), 1.65(s, 3H), 5.24(s, 1H), 7.20-7.64(m, 10H), 8.0(s, 1H).

39
- 0000209044
- and references cited therein;
- (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745 and references cited therein;
- (1999) Chem. Rev , vol.99 , pp. 745
- Krief, A.¹ Laval, A.-M.²

40
- 0032473838
- (b) Molander G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321;
- (1998) Tetrahedron , vol.54 , pp. 3321
- Molander, G.A.¹ Harris, C.R.²

41
- 46149125694
- Molander G. A. in Organic Reactions, ed. Paquette, L. A., John Wiley & Sons: New York, 1994, 46, pp. 211;
- (c) Molander G. A. in Organic Reactions, ed. Paquette, L. A., John Wiley & Sons: New York, 1994, vol. 46, pp. 211; (

42
- 0010077452
- d) Molander G. A. Chem. Rev. 1992, 92, 29.
- (1992) Chem. Rev , vol.92 , pp. 29
- Molander, G.A.¹

43
- 46149105131
- 4, and evaporated in vacuo to provide crude products which was purified by preparative TLC (petroleum ether/ethyl acetate 3:1) to give 4a and 5a.
- 4, and evaporated in vacuo to provide crude products which was purified by preparative TLC (petroleum ether/ethyl acetate 3:1) to give 4a and 5a.

44
- 46149088619
- 3): δ, 1-10 (s, 3H), 1.31 (d, J= 6.5, 3H), 1.60 (s, 3H), 4.11 (q, J= 6.5, 1H), 5.42 (s, 1H), 7.12-7.40 (m, 10H), 7.53 (s, 1H).
- 3): δ, 1-10 (s, 3H), 1.31 (d, J= 6.5, 3H), 1.60 (s, 3H), 4.11 (q, J= 6.5, 1H), 5.42 (s, 1H), 7.12-7.40 (m, 10H), 7.53 (s, 1H).

45
- 46149090508
- 3): δ, 0.95 (t, J=6.3, 3H), 1.10 (s, 3H), 1.34 (m, 2H), 1.60 (s, 3H), 3.93 (t, J= 6.6, 1H), 5.44 (a, 1H), 7.12-7.40 (m, 10H), 7.60 (s, 1H).
- 3): δ, 0.95 (t, J=6.3, 3H), 1.10 (s, 3H), 1.34 (m, 2H), 1.60 (s, 3H), 3.93 (t, J= 6.6, 1H), 5.44 (a, 1H), 7.12-7.40 (m, 10H), 7.60 (s, 1H).

46
- 46149101693
- 3): δ, 0.95 (s, 3H), 1.07 (s, 9H), 1.62 (s, 3H), 3.90 (s, 1H), 5.47 (s, 1H, 7.07-7.32 (m, 10H), 7.55 (s, 1H).
- 3): δ, 0.95 (s, 3H), 1.07 (s, 9H), 1.62 (s, 3H), 3.90 (s, 1H), 5.47 (s, 1H, 7.07-7.32 (m, 10H), 7.55 (s, 1H).

47
- 46149083648
- 3): δ, 0.96 (s, 3H), 1.06 (d, J= 6.5, 6H), 1.45 (m, 2H), 1.60 (s, 3H), 1.87 (m, 2H), 3.95 (m, 1H), 5.46 (a, 1H), 7.12-7.34 (m: 10H), 7.59 (s, 1H).
- 3): δ, 0.96 (s, 3H), 1.06 (d, J= 6.5, 6H), 1.45 (m, 2H), 1.60 (s, 3H), 1.87 (m, 2H), 3.95 (m, 1H), 5.46 (a, 1H), 7.12-7.34 (m: 10H), 7.59 (s, 1H).

48
- 46149097561
- 3): δ, 0.93 (s, 3H), 1.06 (d, J= 6.5, 6H), 1.63 (s, 3H), 1.96 (m, 1H), 3.90 (d, J= 6.6, 1H), 5.45 (s, 1H), 7.10-7.35 (m, 10H), 7.64 (s, 1H).
- 3): δ, 0.93 (s, 3H), 1.06 (d, J= 6.5, 6H), 1.63 (s, 3H), 1.96 (m, 1H), 3.90 (d, J= 6.6, 1H), 5.45 (s, 1H), 7.10-7.35 (m, 10H), 7.64 (s, 1H).

49
- 46149115556
- 3): δ, 0.94 (s, 3H), 0.98 (t, J= 6.4, 3H), 1.33 (m, 2H), 1.50 (m, 2H), 1.66 (s, 3H), 3.94 (m, 1H), 5.47 (s, 1H), 7.09-7.33 (m, 10H), 7.60 (s, 1H).
- 3): δ, 0.94 (s, 3H), 0.98 (t, J= 6.4, 3H), 1.33 (m, 2H), 1.50 (m, 2H), 1.66 (s, 3H), 3.94 (m, 1H), 5.47 (s, 1H), 7.09-7.33 (m, 10H), 7.60 (s, 1H).

50
- 46149090739
- 3): δ, 1.10 (s, 3H), 1.31 (d, J= 6.5, 3H), 1.62 (s, 3H), 4.11 (q, J= 6.5, IH), 5.46 (a, 1H), 7.12-7.40 (m, 10H), 7.55 (s, 1H).
- 3): δ, 1.10 (s, 3H), 1.31 (d, J= 6.5, 3H), 1.62 (s, 3H), 4.11 (q, J= 6.5, IH), 5.46 (a, 1H), 7.12-7.40 (m, 10H), 7.55 (s, 1H).

51
- 46149126800
- 3): δ, 0.99 (t, J=6.3, 3H), 1.12 (s, 3H), 1.35 (m, 2H), 1.63 (s, 3H), 3.95 (t, J= 6.6, 1H), 5.47 (a, 1H), 7.12-7.40 (m, 10H), 7.62 (s, 1H).
- 3): δ, 0.99 (t, J=6.3, 3H), 1.12 (s, 3H), 1.35 (m, 2H), 1.63 (s, 3H), 3.95 (t, J= 6.6, 1H), 5.47 (a, 1H), 7.12-7.40 (m, 10H), 7.62 (s, 1H).

52
- 46149125439
- 3): δ, 0.96 (s, 3H), 1.10 (s, 9H), 1.64 (s, 3H), 3.93 (s, 1H, 5.50 (s, 1H), 7.10-7.32 (m, 10H), 7.57 (a, 1H).
- 3): δ, 0.96 (s, 3H), 1.10 (s, 9H), 1.64 (s, 3H), 3.93 (s, 1H, 5.50 (s, 1H), 7.10-7.32 (m, 10H), 7.57 (a, 1H).

53
- 46149120039
- 3): δ, 0.98 (s, 3H), 1.10 (d, J= 6.5, 6H), 1.47 (m, 2H), 1.61 (s, 3H), 1.88 (m, 1H), 3.97 (m, 1H), 5.49, (s, 1H), 7.10-7.38 (m, 10H), 7.62 (s, 1H).
- 3): δ, 0.98 (s, 3H), 1.10 (d, J= 6.5, 6H), 1.47 (m, 2H), 1.61 (s, 3H), 1.88 (m, 1H), 3.97 (m, 1H), 5.49, (s, 1H), 7.10-7.38 (m, 10H), 7.62 (s, 1H).

54
- 46149098266
- 3): δ, 0.94 (s, 3H), 1.09 (d, J= 6.5, 6H), 1.67 (s, 3H), 1.92 (m, 1H), 3.92 (d, J= 6.6, 1H), 5.48 (s, 1H), 7.08-7.34 (m, 10H), 7.66 (s, 1H).
- 3): δ, 0.94 (s, 3H), 1.09 (d, J= 6.5, 6H), 1.67 (s, 3H), 1.92 (m, 1H), 3.92 (d, J= 6.6, 1H), 5.48 (s, 1H), 7.08-7.34 (m, 10H), 7.66 (s, 1H).

55
- 46149096660
- 3): δ, 0.95 (s, 3H), 0.99 (t, J= 6.4, 3H), 1.35 (m, 2H), 1.51 (m, 2H), 1.68 (s, 3H), 3.95 (m, 1H), 5.49 (s, 1H) 7.06-7.30 (m, 10H), 7.62 (s, 1H).
- 3): δ, 0.95 (s, 3H), 0.99 (t, J= 6.4, 3H), 1.35 (m, 2H), 1.51 (m, 2H), 1.68 (s, 3H), 3.95 (m, 1H), 5.49 (s, 1H) 7.06-7.30 (m, 10H), 7.62 (s, 1H).

56
- 0001311213
- (a) Hruby, V. J.; Russell, K. C. and Nicolas, E. J. Org. Chem. 1993, 58, 766;
- (1993) J. Org. Chem , vol.58 , pp. 766
- Hruby, V.J.¹ Russell, K.C.² Nicolas, E.³

57
- 0001322727
- (b) Lou, B.; Li, G.; Lung, F. and Hurby, V. J. J. Org. Chem. 1995, 60, 5509.
- (1995) J. Org. Chem , vol.60 , pp. 5509
- Lou, B.¹ Li, G.² Lung, F.³ Hurby, V.J.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.