SCOPUS 정보 검색 플랫폼

Volumn , Issue 17, 2008, Pages 2609-2612

Ethyl 5-[(4-methylphenyl)sulfonyl]-3-oxopentanoate: A bench-stable synthon for ethyl 3-oxopent-4-enoate (Nazarov's Reagent)

(6) Benetti, Simonetta a Carli, Stefano b De Risi, Carmela b Pollini, Gian P b Veronese, Augusto C b Zanirato, Vinicio b

a Dipartimento di Matematica (Italy)

b Dipartimento di Scienze Farmaceutiche (Italy)

Author keywords

Annulations; Bicyclic compounds; Carbocycles; Nazarov's reagent; Tandem reactions

Indexed keywords

ACRYLIC ACID; ACRYLONITRILE; ETHYL 3 OXOPENT 4 ENOATE; ETHYL 5 [(4 METHYLPHENYL)SULFONYL] 3 OXOPENTANOATE; SODIUM 4 TOLUENESULFINATE; SULFINIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ANNULATION REACTION; ARTICLE; CONTROLLED STUDY; ELIMINATION REACTION;

EID: 55449103442 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083378 Document Type: Article

Times cited : (6)

References (41)

1
- 0000634134
- (a) Nazarov, I. N.; Zav'yalov, S. I. Zh. Obshch. Khim. 1953, 23, 1703;
- (1953) Zh. Obshch. Khim , vol.23 , pp. 1703
- Nazarov, I.N.¹ Zav'yalov, S.I.²

2
- 55449120949
- J. Gen. Chem. USSR; 1953, 23, 1793;
- (1953) J. Gen. Chem. USSR , vol.23 , pp. 1793

3
- 33750286079
- Chem. Abstr. 1954, 48, 13667h.
- (1954) Chem. Abstr , vol.48

4
- 33750499738
- (b) Kaur, T. Synlett 2006, 2853.
- (2006) Synlett , pp. 2853
- Kaur, T.¹

5
- 0001890477
- (a) Nominé, G.; Amiard, G.; Torelli, V. Bull. Soc. Chim. Fr. 1968, 3664.
- (1968) Bull. Soc. Chim. Fr , pp. 3664
- Nominé, G.¹ Amiard, G.² Torelli, V.³

6
- 84971073673
- (b) Collins, D. J.; Tomkins, C. W. Aust. J. Chem. 1977, 30, 443.
- (1977) Aust. J. Chem , vol.30 , pp. 443
- Collins, D.J.¹ Tomkins, C.W.²

7
- 0019947610
- (c) Caselli, A. S.; Collins, D. J.; Stone, G. M. Aust. J. Chem. 1982, 35, 799.
- (1982) Aust. J. Chem , vol.35 , pp. 799
- Caselli, A.S.¹ Collins, D.J.² Stone, G.M.³

8
- 0029162768
- (d) Watson, A. T.; Park, K.; Wiemer, D. F.; Scott, W. J. J. Org. Chem. 1995, 60, 5102.
- (1995) J. J. Org. Chem , vol.60 , pp. 5102
- Watson, A.T.¹ Park, K.² Wiemer, D.F.³ Scott, W.⁴

9
- 0035966238
- (e) Ling, T.; Chowdhury, C.; Kramer, B. A.; Vong, B. G.; Palladino, M. A.; Theodorakis, E. A. J. Org. Chem. 2001, 66, 8843.
- (2001) J. Org. Chem , vol.66 , pp. 8843
- Ling, T.¹ Chowdhury, C.² Kramer, B.A.³ Vong, B.G.⁴ Palladino, M.A.⁵ Theodorakis, E.A.⁶

10
- 1642569134
- (f) Ghosh, S.; Rivas, F.; Fischer, D.; González, M. A.; Theodorakis, E. A. Org. Lett. 2004, 6, 941.
- (2004) Org. Lett , vol.6 , pp. 941
- Ghosh, S.¹ Rivas, F.² Fischer, D.³ González, M.A.⁴ Theodorakis, E.A.⁵

11
- 0007705262
- Schkeryantz, J. M.; Luly, J. R.; Coghlan, M. J. Synlett 1998, 723.
- (1998) Synlett , pp. 723
- Schkeryantz, J.M.¹ Luly, J.R.² Coghlan, M.J.³

12
- 49549127411
- (a) Könst, W. M. B.; Witteveen, J. G.; Boelens, H. Tetrahedron 1976, 32, 1415.
- (1976) Tetrahedron , vol.32 , pp. 1415
- Könst, W.M.B.¹ Witteveen, J.G.² Boelens, H.³

13
- 55449138308
- (b) Orsini, F.; Pelizzoni, F.; Destro, R. Gazz. Chim. Ital. 1978,108, 693.
- (1978) Gazz. Chim. Ital , vol.108 , pp. 693
- Orsini, F.¹ Pelizzoni, F.² Destro, R.³

14
- 0006452120
- (a) Célérier, J.-P.; Eskénazi, C.; Lhommet, G.; Maitte, P. J. Heterocycl. Chem. 1979, 16, 953.
- (1979) J. Heterocycl. Chem , vol.16 , pp. 953
- Célérier, J.-P.¹ Eskénazi, C.² Lhommet, G.³ Maitte, P.⁴

15
- 0000475435
- (b) Watanabe, T.; Nakashita, Y.; Katayama, S.; Yamauchi, M. Heterocycles 1980, 14, 1433.
- (1980) Heterocycles , vol.14 , pp. 1433
- Watanabe, T.¹ Nakashita, Y.² Katayama, S.³ Yamauchi, M.⁴

16
- 0346887162
- (c) Jong, L.; Zaveri, N.; Toll, L. Bioorg. Med. Chem. Lett. 2004, 14, 181.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 181
- Jong, L.¹ Zaveri, N.² Toll, L.³

17
- 0027052359
- and references cited therein
- Dodd, D. S.; Oehlschlager, A. C.; Georgopapadakou, N. H.; Polak, A.-M.; Hartman, P. G. J. Org. Chem. 1992, 57, 7226; and references cited therein.
- (1992) J. Org. Chem , vol.57 , pp. 7226
- Dodd, D.S.¹ Oehlschlager, A.C.² Georgopapadakou, N.H.³ Polak, A.-M.⁴ Hartman, P.G.⁵

18
- 0028029641
- Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Romagnoli, R.; Zanirato, V. Tetrahedron Lett. 1994, 35, 9297.
- (1994) Tetrahedron Lett , vol.35 , pp. 9297
- Albertini, E.¹ Barco, A.² Benetti, S.³ De Risi, C.⁴ Pollini, G.P.⁵ Romagnoli, R.⁶ Zanirato, V.⁷

19
- 84918262000
- (a) Gelin, S.; Gelin, R. Bull. Soc. Chim. Fr. 1969, 4091.
- (1969) Bull. Soc. Chim. Fr , pp. 4091
- Gelin, S.¹ Gelin, R.²

20
- 84987201623
- (b) Pichat, L.; Beaucourt, J.-P. Synthesis 1973, 537.
- (1973) Synthesis , pp. 537
- Pichat, L.¹ Beaucourt, J.-P.²

21
- 0000569691
- (c) Trost, B. M.; Kunz, R. A. J. Org. Chem. 1974, 39, 2648.
- (1974) J. Org. Chem , vol.39 , pp. 2648
- Trost, B.M.¹ Kunz, R.A.²

22
- 84950035077
- (d) Ohta, S.; Shimabayashi, A.; Hatano, S.; Okamoto, M. Synthesis 1983, 715.
- (1983) Synthesis , pp. 715
- Ohta, S.¹ Shimabayashi, A.² Hatano, S.³ Okamoto, M.⁴

23
- 0001400053
- (a) Wenkert, E.; Ceccherelli, P.; Fugiel, R. A. J. Org. Chem. 1978. 43, 3982.
- (1978) J. Org. Chem , vol.43 , pp. 3982
- Wenkert, E.¹ Ceccherelli, P.² Fugiel, R.A.³

24
- 37049094178
- (b) Pellicciari, R.; Fringuelli, R.; Ceccherelli, P.; Sisani, E. J. Chem. Soc., Chem. Commun. 1979, 959.
- (1979) J. Chem. Soc., Chem. Commun , pp. 959
- Pellicciari, R.¹ Fringuelli, R.² Ceccherelli, P.³ Sisani, E.⁴

25
- 0000946337
- (c) Padwa, A.; Kulkarni, Y. S.; Zhang, Z. J. Org. Chem. 1990, 55, 4144.
- (1990) J. Org. Chem , vol.55 , pp. 4144
- Padwa, A.¹ Kulkarni, Y.S.² Zhang, Z.³

26
- 0002545840
- Stork, G.; Guthikonda, R. N. Tetrahedron Lett. 1972, 27, 2755.
- (1972) Tetrahedron Lett , vol.27 , pp. 2755
- Stork, G.¹ Guthikonda, R.N.²

27
- 0000945724
- (a) Zibuck, R.; Streiber, J. M. J. Org. Chem. 1989, 54, 4717.
- (1989) J. Org. Chem , vol.54 , pp. 4717
- Zibuck, R.¹ Streiber, J.M.²

28
- 0000520370
- (b) Zibuck, R.; Streiber, J. M. Org. Synth. 1993, 71, 236.
- (1993) Org. Synth , vol.71 , pp. 236
- Zibuck, R.¹ Streiber, J.M.²

29
- 0032497666
- (a) Barco, A.; Benetti, S.; De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. Tetrahedron Lett. 1998, 39, 7591.
- (1998) Tetrahedron Lett , vol.39 , pp. 7591
- Barco, A.¹ Benetti, S.² De Risi, C.³ Marchetti, P.⁴ Pollini, G.P.⁵ Zanirato, V.⁶

30
- 38349020764
- (b) Barco, A.; Benetti, S.; De Risi, C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. Eur. J. Org. Chem. 2001, 975.
- (2001) Eur. J. Org. Chem , pp. 975
- Barco, A.¹ Benetti, S.² De Risi, C.³ Marchetti, P.⁴ Pollini, G.P.⁵ Zanirato, V.⁶

31
- 55449112310
- Typical Procedures for the Preparation of Compound 2 Method A: A stirred suspension of zinc dust (3.8 g, 58.1 mmol) in THF (28 mL) was treated with MsOH (0.14 mL, 2.2 mmol) and heated at reflux for 10 min. Ethyl bromoacetate (1.0 mL, 9.0 mmol) was added dropwise until it turned green, then 3 (4.0 g, 19.1 mmol) was added. Ethyl bromoacetate (4.0 mL, 36.1 mmol) was successively dropped over a period of 30 min. The reaction mixture was refluxed for 3 h, cooled to 0 °C, and treated with 10% HCl (28 mL, The solution was stirred at r.t. for 2 h, then the solvent was concentrated in vacuo. The residue was extracted with EtOAc (3 × 60 mL, the combined organic phases were washed with brine (2 × 100 mL, and dried (Na2SO4, The solvent was evaporated, and the residue was purified by flash chromatography (EtOAc-PE, 1:2) to afford 2 (4.3 g, 75, Method B: 1,1′-Carbonyldiimidazole (3.5 g, 21.6 mmol) was added to a solution of the a
- 4). Evaporation of the solvent and purification of the oily residue by flash chromatography (EtOAc-PE, 1:2) gave 2 (4.2 g, 80%).

32
- 5344255439
- Kamogawa, H.; Kusaka, H.; Nanasawa, M. Bull. Chem. Soc. Jpn. 1980, 53, 3379.
- (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 3379
- Kamogawa, H.¹ Kusaka, H.² Nanasawa, M.³

33
- 0001328519
- Bonete, P.; Nájera, C. J. Org. Chem. 1994, 59, 3202.
- (1994) J. Org. Chem , vol.59 , pp. 3202
- Bonete, P.¹ Nájera, C.²

34
- 8744253296
- Shin, H.; Choi, B. S.; Lee, K. K.; Choi, H.-w.; Chang, J. H.; Lee, K. W.; Nam, D. H.; Kim, N.-S. Synthesis 2004, 2629.
- (2004) Synthesis , pp. 2629
- Shin, H.¹ Choi, B.S.² Lee, K.K.³ Choi, H.-W.⁴ Chang, J.H.⁵ Lee, K.W.⁶ Nam, D.H.⁷ Kim, N.-S.⁸

35
- 84969808662
- Brooks, D. W.; Lu, L. D.-L.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1979, 18, 72.
- (1979) Angew. Chem., Int. Ed. Engl , vol.18 , pp. 72
- Brooks, D.W.¹ Lu, L.D.-L.² Masamune, S.³

36
- 55449083276
- 5S: C, 56.36; H, 6.08. Found: C, 56.20; H, 6.23.
- 5S: C, 56.36; H, 6.08. Found: C, 56.20; H, 6.23.

37
- 55449115251
- Typical Procedure for the Preparation of Compound 6 A solution of 2 (0.2 g, 0.67 mmol) and KF (0.16 g, 2.75 mmol) in MeOH (10 mL) was stirred at r.t. for 12 h. The solvent was evaporated under reduced pressure, and the crude residue was purified by flash chromatography (EtOAc-PE, 1:3) yielding 6 as a colorless oil (76 mg, 40, IR: 3474, 1697, 1655, 1584 cm-1. 1H NMR (400 MHz, CDCl3, δ, 1.27 (t, J, 7.2 Hz, 3 H, 1.32 (t, J, 7.2 Hz, 3 H, 1.72-1.84 (m, 1 H, 1.90-2.00 (m, 1 H, 2.18-2.30 (m, 1 H, 2.48-2.52 (m, 1 H, 2.53-2.58 (m, 2 H, 4.13-4.30 (m, 4 H, 4.47 (s, 1 H, 5.73 (s, 1 H, 6.02 (s, 1 H, 12.09 (s, enol OH, 13C NMR 100 MHz, CDCl3, δ =14.13, 14.24, 19.95, 34.02, 42.04, 60.81, 61.06, 71.04, 97.80, 115.83, 143.56, 162.24, 172.52. Anal. Calcd for C14H20O6: C, 59.14; H, 7.09. Found: C, 59.20; H, 7.00
- 6: C, 59.14; H, 7.09. Found: C, 59.20; H, 7.00.

38
- 41649086484
- and references cited therein
- Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511; and references cited therein.
- (2008) Tetrahedron , vol.64 , pp. 4511
- Singh, V.¹ Batra, S.²

39
- 37549037472
- For an organocatalytic asymmetric tandem Michael and Morita-Baylis- Hillman reaction between α,β-unsaturated aldehydes and Nazarov's reagents leading to cyclohexane derivatives structurally related to 6, see: Cabrera, S.; Alemán, J.; Bolze, P.; Bertelsen, S.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2008, 47, 121.
- For an organocatalytic asymmetric tandem Michael and Morita-Baylis- Hillman reaction between α,β-unsaturated aldehydes and Nazarov's reagents leading to cyclohexane derivatives structurally related to 6, see: Cabrera, S.; Alemán, J.; Bolze, P.; Bertelsen, S.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2008, 47, 121.

40
- 55449120104
- Selected Analytical Data for Compounds 10a and 10b Compound 10a: colorless oil. IR: 1706, 1650, 1620, 1545 cm-1. 1H NMR (400 MHz, CDCl3, δ (less polar isomer, 0.95 (t, J, 7.2 Hz, 3 H, 2.00-2.12 (m, 1 H, 2.36-2.70 (m, 3 H, 3.96-4.08 (m, 2 H, 4.56-4.63 (m, 1 H, 4.70-4.76 (br, 1 H, 7.17-7.37 (m, 5 H, 12.55 (s, enol OH, 13C NMR (100 MHz, CDCl3, δ (less polar isomer, 13.70, 20.87, 24.83, 42.46, 60.62, 85.99, 96.79, 127.31, 127.60, 128.77, 141.34, 171.41. Anal. Calcd for C15H17NO5: C, 61.85; H, 5.88. Found: C, 61.91; H, 5.80. Compound 10b: colorless oil. IR: 1710, 1660, 1610, 1550 cm-1. 1H NMR (400 MHz, CDCl 3, δ (more polar isomer, 0.96 (t, J= 7.2 Hz, 3 H, 2.00-2.13 (m, 1 H, 2.40-2.76 (m, 3 H, 3.93-4.10 (m, 2 H, 4.50-1.60 (m, 1 H, 4.70-4.80 (br, 1 H, 7.20-7.30 (m, 1 H, 7.46-7.53 (m, 1 H, 8.46-8.56 br
- 5: C, 57.53; H, 5.52. Found C, 57.50; H, 5.60.

41
- 28944450864
- Hoashi, Y.; Yabuta, T.; Yuan, P.; Miyabe, H.; Takemoto, Y. Tetrahedron 2006, 62, 365.
- (2006) Tetrahedron , vol.62 , pp. 365
- Hoashi, Y.¹ Yabuta, T.² Yuan, P.³ Miyabe, H.⁴ Takemoto, Y.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.