SCOPUS 정보 검색 플랫폼

Volumn 60, Issue 27, 2004, Pages 5793-5798

SmI2-mediated elimination reaction of Baylis-Hillman adducts controlled by temperature: A facile synthesis of trisubstituted alkenes and 1,5-hexadiene derivatives with E-stereoselectivity

(3) Li, Jian a Qian, Weixing a Zhang, Yongmin a,b

a ZHEJIANG UNIVERSITY (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

(E) stereoselectivity; 1,5 Hexadiene derivatives; Baylis Hillman adducts; Elimination; Reduction; Samarium diiodide; Self coupling; Trisubstituted alkene

Indexed keywords

ALKADIENE; ALKENE; SAMARIUM DIIODIDE;

ARTICLE; BAYLIS HILLMAN REACTION; ELIMINATION REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 2942517900 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/j.tet.2004.04.087 Document Type: Article

Times cited : (35)

References (43)

1
- 0000404060
- Marfat A., McGuirk P.R., Helquist P. J. Org. Chem. 44:1979;3888-3901
- (1979) J. Org. Chem. , vol.44 , pp. 3888-3901
- Marfat, A.¹ McGuirk, P.R.² Helquist, P.³

2
- 0031032858
- Anderson R.J., Coleman J.E., Piers E., Wallace D.J. Tetrahedron Lett. 38:1997;317-320
- (1997) Tetrahedron Lett. , vol.38 , pp. 317-320
- Anderson, R.J.¹ Coleman, J.E.² Piers, E.³ Wallace, D.J.⁴

3
- 0023264587
- Tanaka H., Kuroda A., Marusawa H., Hatanaka H., Kino T., Goto T., Hashimoto M. J. Am. Chem. Soc. 109:1987;5031-5033
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5031-5033
- Tanaka, H.¹ Kuroda, A.² Marusawa, H.³ Hatanaka, H.⁴ Kino, T.⁵ Goto, T.⁶ Hashimoto, M.⁷

4
- 0029876114
- Ishibashi Y., Ohba S., Nishiyama S., Yamamura S. Tetrahedron Lett. 37:1996;2997-3000
- (1996) Tetrahedron Lett. , vol.37 , pp. 2997-3000
- Ishibashi, Y.¹ Ohba, S.² Nishiyama, S.³ Yamamura, S.⁴

5
- 0028997861
- Senokuchi K., Nakai H., Nakayama Y., Odagaki Y., Sakaki K., Kato M., Maruyama T., Miyazaki T., Ito H., Kamiyasu K., Kim S., Kawamura M., Hamanaka N. J. Med. Chem. 38:1995;2521-2523
- (1995) J. Med. Chem. , vol.38 , pp. 2521-2523
- Senokuchi, K.¹ Nakai, H.² Nakayama, Y.³ Odagaki, Y.⁴ Sakaki, K.⁵ Kato, M.⁶ Maruyama, T.⁷ Miyazaki, T.⁸ Ito, H.⁹ Kamiyasu, K.¹⁰ Kim, S.¹¹ Kawamura, M.¹² Hamanaka, N.¹³

6
- 0018903576
- Watanabe T., Hayashi K., Yoshimatsu S., Sakai K., Takeyama S., Takashima K. J. Med. Chem. 23:1980;50-59
- (1980) J. Med. Chem. , vol.23 , pp. 50-59
- Watanabe, T.¹ Hayashi, K.² Yoshimatsu, S.³ Sakai, K.⁴ Takeyama, S.⁵ Takashima, K.⁶

7
- 84989585272
- Denmark S.E., Amburgey J. J. Am. Chem. Soc. 115:1993;10386-10387
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 10386-10387
- Denmark, S.E.¹ Amburgey, J.²

8
- 0000340698
- Kocienski P., Dixon N.J., Wadman S. Tetrahedron Lett. 29:1988;2353-2356
- (1988) Tetrahedron Lett. , vol.29 , pp. 2353-2356
- Kocienski, P.¹ Dixon, N.J.² Wadman, S.³

9
- 0001286010
- Myers A.G., Kukkola P.J. J. Am. Chem. Soc. 112:1990;8208-8210
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 8208-8210
- Myers, A.G.¹ Kukkola, P.J.²

10
- 0028067332
- Creton I., Marek I., Brasseur D., Jestin J.-L., Normant J.-F. Tetrahedron Lett. 35:1994;6873-6876
- (1994) Tetrahedron Lett. , vol.35 , pp. 6873-6876
- Creton, I.¹ Marek, I.² Brasseur, D.³ Jestin, J.-L.⁴ Normant, J.-F.⁵

11
- 0000892247
- For reviews, see: (a)
- For reviews, see: (a) Ciganek E. Org. React. 51:1997;201-350
- (1997) Org. React. , vol.51 , pp. 201-350
- Ciganek, E.¹

12
- 0342419508
- Basavaiah D., Rao P.D., Hyma R.S. Tetrahedron. 52:1996;8001-8062
- (1996) Tetrahedron , vol.52 , pp. 8001-8062
- Basavaiah, D.¹ Rao, P.D.² Hyma, R.S.³

13
- 0037366617
- Basavaiah D., Rao A.J., Satyanarayana T. Chem. Rev. 103:2003;811-892
- (2003) Chem. Rev. , vol.103 , pp. 811-892
- Basavaiah, D.¹ Rao, A.J.² Satyanarayana, T.³

14
- 0001490739
- For examples: (a)
- For examples: (a) Kim J.N., Lee H.J., Lee K.Y., Gong J.H. Synlett. 2002;173-175
- (2002) Synlett , pp. 173-175
- Kim, J.N.¹ Lee, H.J.² Lee, K.Y.³ Gong, J.H.⁴

15
- 0036422096
- Patra A., Roy A.K., Batra S., Bhaduri A.P. Synlett. 2003;1819-1822
- (2003) Synlett , pp. 1819-1822
- Patra, A.¹ Roy, A.K.² Batra, S.³ Bhaduri, A.P.⁴

16
- 0242628820
- Kabalka G.W., Venkataiah B., Dong G. Org. Lett. 5:2003;3803-3805
- (2003) Org. Lett. , vol.5 , pp. 3803-3805
- Kabalka, G.W.¹ Venkataiah, B.² Dong, G.³

17
- 0038778548
- Kabalka G.W., Venkataiah B., Dong G. Tetrahedron Lett. 44:2003;4673-4675
- (2003) Tetrahedron Lett. , vol.44 , pp. 4673-4675
- Kabalka, G.W.¹ Venkataiah, B.² Dong, G.³

18
- 0035905005
- Chung Y.M., Gong J.H., Kim T.H., Kim J.N. Tetrahedron Lett. 42:2001;9023-9026
- (2001) Tetrahedron Lett. , vol.42 , pp. 9023-9026
- Chung, Y.M.¹ Gong, J.H.² Kim, T.H.³ Kim, J.N.⁴

19
- 37049085258
- Basavaiah D., Sarma P.K.S. J. Chem. Soc., Chem. Commun. 1992;955-957
- (1992) J. Chem. Soc., Chem. Commun. , pp. 955-957
- Basavaiah, D.¹ Sarma, P.K.S.²

20
- 18244387510
- Hoffmann H.M.R., Rabe J. J. Org. Chem. 50:1985;3849-3859
- (1985) J. Org. Chem. , vol.50 , pp. 3849-3859
- Hoffmann, H.M.R.¹ Rabe, J.²

21
- 0032560778
- Pachamuthu K., Vankar Y.D. Tetrahedron Lett. 39:1998;5439-5442
- (1998) Tetrahedron Lett. , vol.39 , pp. 5439-5442
- Pachamuthu, K.¹ Vankar, Y.D.²

22
- 0033582757
- Basavaiah D., Krishnamacharyulu M., Hyma R.S., Sarma P.K.S., Kumaragurubaran N. J. Org. Chem. 64:1999;1197-1200
- (1999) J. Org. Chem. , vol.64 , pp. 1197-1200
- Basavaiah, D.¹ Krishnamacharyulu, M.² Hyma, R.S.³ Sarma, P.K.S.⁴ Kumaragurubaran, N.⁵

23
- 0035927240
- Shadakshari U., Nayak S.K. Tetrahedron. 57:2001;4599-4602
- (2001) Tetrahedron , vol.57 , pp. 4599-4602
- Shadakshari, U.¹ Nayak, S.K.²

24
- 33847086035
- For reviews and representative examples, see: (a)
- For reviews and representative examples, see: (a) Girard P., Namy J.L., Kagan H.B. J. Am. Chem. Soc. 102:1980;2693-2698
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693-2698
- Girard, P.¹ Namy, J.L.² Kagan, H.B.³

25
- 0000209044
- Krief A., Laval A.M. Chem. Rev. 99:1999;745-777
- (1999) Chem. Rev. , vol.99 , pp. 745-777
- Krief, A.¹ Laval, A.M.²

26
- 0542397750
- Molander G.A. Acc. Chem. Res. 31:1998;603-609
- (1998) Acc. Chem. Res. , vol.31 , pp. 603-609
- Molander, G.A.¹

27
- 0032473838
- Molander G.A., Harris C.R. Tetrahedron. 54:1998;3321-3354
- (1998) Tetrahedron , vol.54 , pp. 3321-3354
- Molander, G.A.¹ Harris, C.R.²

28
- 2142715741
- Molander G.A., Harris C.R. Chem. Rev. 96:1996;307-338
- (1996) Chem. Rev. , vol.96 , pp. 307-338
- Molander, G.A.¹ Harris, C.R.²

29
- 0010077452
- Molander G.A. Chem. Rev. 92:1992;29-68
- (1992) Chem. Rev. , vol.92 , pp. 29-68
- Molander, G.A.¹

30
- 0033549735
- Selected references: (a)
- Selected references: (a) Concellón J.M., Bernad P.J., Pére-Andrés J.A. Angew. Chem., Int. Ed. 38:1999;2384-2386
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2384-2386
- Concellón, J.M.¹ Bernad, P.J.² Pére-Andrés, J.A.³

31
- 0040184024
- Concellón J.M., Bernad P.J., Pére-Andrés J.A., Rodríguez-Solla H. Angew. Chem., Int. Ed. 39:2000;2773-2775
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2773-2775
- Concellón, J.M.¹ Bernad, P.J.² Pére-Andrés, J.A.³ Rodríguez-Solla, H.⁴

32
- 0001114037
- Concellón J.M., Bardales E. Org. Lett. 4:2002;189-191
- (2002) Org. Lett. , vol.4 , pp. 189-191
- Concellón, J.M.¹ Bardales, E.²

33
- 0000363311
- Concellón J.M., Bernad P.J., Bardales E. Org. Lett. 3:2001;937-939
- (2001) Org. Lett. , vol.3 , pp. 937-939
- Concellón, J.M.¹ Bernad, P.J.² Bardales, E.³

34
- 0037463460
- Concellón J.M., Huerta M. Tetrahedron Lett. 44:2003;1931-1934
- (2003) Tetrahedron Lett. , vol.44 , pp. 1931-1934
- Concellón, J.M.¹ Huerta, M.²

35
- 0345603775
- Li J., Xu X.L., Zhang Y.M. Tetrahedron Lett. 44:2003;9349-9351
- (2003) Tetrahedron Lett. , vol.44 , pp. 9349-9351
- Li, J.¹ Xu, X.L.² Zhang, Y.M.³

36
- 2942536569
- 13C NMR spectral analyses indicate the absence of any (Z)-isomer
- 13C NMR spectral analyses indicate the absence of any (Z)-isomer

37
- 2942538404
- note
- 13C NMR are quite in analog with 3d. The E-stereochemistry of 2d can be easily explained according to the following mechanism proposed (Scheme 2)

38
- 2942534663
- 8 The E-configuration of 3b was also further assigned by a 2D NOESY experiment

39
- 0033537046
- Dumond Y., Negishi E.-I. J. Am. Chem. Soc. 121:1999;11223-11224
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11223-11224
- Dumond, Y.¹ Negishi, E.-I.²

40
- 0010301210
- McMurry J.E., Silvsstri M. J. Org. Chem. 40:1975;2687-2688
- (1975) J. Org. Chem. , vol.40 , pp. 2687-2688
- McMurry, J.E.¹ Silvsstri, M.²

41
- 0040184024
- 2: (a)
- 2: (a) Concellón J.M., Bernad P.J., Pére-Andrés J.A., Rodríguez-Solla H. Angew. Chem., Int. Ed. 39:2000;2773-2775
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2773-2775
- Concellón, J.M.¹ Bernad, P.J.² Pére-Andrés, J.A.³ Rodríguez-Solla, H.⁴

42
- 0000363311
- Concellón J.M., Bernad P.J., Bardales E. Org. Lett. 3:2001;937-939
- (2001) Org. Lett. , vol.3 , pp. 937-939
- Concellón, J.M.¹ Bernad, P.J.² Bardales, E.³

43
- 84985531959
- All Baylis-Hillman adducts are prepared from aromatic aldehydes and methyl acrylate according to literature:
- All Baylis-Hillman adducts are prepared from aromatic aldehydes and methyl acrylate according to literature: Hoffman H.M.R., Rabe J. Angew. Chem., Int. Ed. 22:1983;795-796
- (1983) Angew. Chem., Int. Ed. , vol.22 , pp. 795-796
- Hoffman, H.M.R.¹ Rabe, J.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.