SCOPUS 정보 검색 플랫폼

Tetrahedron

Volumn 58, Issue 20, 2002, Pages 3855-3864

Fluorous Mitsunobu reagents and reactions

(2) Dandapani, Sivaraman a Curran, Dennis P a

a UNIVERSITY OF PITTSBURGH (United States)

Author keywords

Diethylazodicarboxylate; Fluorous; Mitsunobu; Solid phase extraction; Triphenylphosphine

Indexed keywords

ALCOHOL; BIS(2,2,3,3,4,4,4 HEPTAFLUOROBUTYL)DIAZODICARBOXYLATE; BIS(2,2,3,3,4,4,4 HEPTAFLUOROBUTYL)HYDRAZINE DICARBOXYLATE; BIS(3,3,4,4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL)DIAZODICARBOXYLATE; BIS(3,3,4,4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL)HYDRAZINE DICARBOXYLATE; BIS(4,4,5,5,5 PENTAFLUOROPENTYL)HYDRAZINE DICARBOXYLATE; BIS(4,4,5,5,6,6,7,7,7 NONAFLUOROHEPTYL)DIAZODICARBOXYLATE; BIS(4,4,5,5,6,6,7,7,7 NONAFLUOROHEPTYL)HYDRAZINE DICARBOXYLATE; BIS(4,4,5,5,6,6,7,7,8,8,9,9,9 TRIDECAFLUORONONYL)DIAZODICARBOXYLATE; BIS(4,4,5,5,6,6,7,7,8,8,9,9,9 TRIDECAFLUORONONYL)HYDRAZINE DICARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; HYDRAZIDE; PHOSPHINE DERIVATIVE; SILICON DIOXIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MITSUNOBU REACTION; OXIDATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REDUCTION; SOLID PHASE EXTRACTION;

EID: 0037071231 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(02)00205-3 Document Type: Article

Times cited : (117)

References (53)

1
- 0001630697
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 1175
- Curran, D.P.¹

2
- 0034583209
- (2000) Pure Appl. Chem. , vol.72 , pp. 1649
- Curran, D.P.¹

3
- 0003520820
- F. Stoddard, D. Reinhoudt, & M. Shibasaki. New York: Wiley-VCH
- (2000) Stimulating Concepts in Chemistry , pp. 25-37
- Curran, D.P.¹

4
- 0038372081
- (1998) Acc. Chem. Res. , vol.31 , pp. 641
- Horvath, I.T.¹

5
- 0033481596
- (1999) Chem. Soc. Rev. , vol.28 , pp. 37
- De Wolf, E.¹ Van Koten, G.² Deelman, B.J.³

6
- 0347243166
- (1999) J. Fluorine Chem. , vol.94 , pp. 183
- Cavazzini, M.¹ Montanari, F.² Pozzi, G.³ Quici, S.⁴

7
- 0033017366
- (1999) Chem. Eur. J. , vol.5 , pp. 1677
- Fish, R.H.¹

8
- 0033303406
- (1999) Coord. Chem. Rev. , vol.192 , pp. 587
- Barthel-Rosa, L.P.¹ Gladysz, J.A.²

9
- 0345982287
- (1999) J. Fluorine Chem. , vol.100 , pp. 75
- Hope, E.G.¹ Stuart, A.M.²

10
- 0002287474
- P. Knochel. Berlin: Springer
- (1999) Modern Solvents in Organic Synthesis , vol.206 , pp. 61
- Betzemeier, B.¹ Knochel, P.²

11
- 0000035623
- (1997) J. Org. Chem. , vol.62 , pp. 6714
- Curran, D.P.¹ Hadida, S.² He, M.³

12
- 0032829737
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9069
- Curran, D.P.¹ Luo, Z.²

13
- 0034731530
- (2000) J. Org. Chem. , vol.65 , pp. 8866
- Zhang, Q.¹ Luo, Z.² Curran, D.P.³

14
- 0034840718
- (2001) Synlett , pp. 1488
- Curran, D.P.¹

15
- 0035874698
- (2001) J. Org. Chem. , vol.66 , pp. 4261
- Luo, Z.¹ Williams, J.² Read, R.W.³ Curran, D.P.⁴

16
- 0030849312
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 7406
- Hadida, S.¹ Super, M.S.² Beckman, E.J.³ Curran, D.P.⁴

17
- 0344565329
- (1997) J. Org. Chem. , vol.62 , pp. 8341
- Hoshino, M.¹ Degenkolb, P.² Curran, D.P.³

18
- 0032497351
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2403
- Curran, D.P.¹ Luo, Z.² Degenkolb, P.³

19
- 0033583294
- (1999) Tetrahedron Lett. , vol.40 , pp. 2367
- Ryu, I.¹ Niguma, T.² Minakata, S.³ Komatsu, M.⁴ Luo, Z.⁵ Curran, D.P.⁶

20
- 0033575413
- (1999) Tetrahedron , vol.55 , pp. 8997
- Curran, D.P.¹ Hadida, S.² Kim, S.Y.³

21
- 0033591868
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6607
- Curran, D.P.¹ Hadida, S.² Kim, S.Y.³ Luo, Z.⁴

22
- 0034597990
- (2000) Tetrahedron Lett. , vol.41 , pp. 9617
- Bucher, B.¹ Curran, D.P.²

23
- 0033580869
- (1999) Tetrahedron Lett. , vol.40 , pp. 4649
- Wipf, P.¹ Reeves, J.T.²

24
- 0033618301
- (1999) Tetrahedron Lett. , vol.40 , pp. 5667
- Rover, S.¹ Wipf, P.²

25
- 0003844243
- (1999) Org. Lett. , pp. 1253
- Wipf, P.¹ Methot, J.-L.²

26
- 0034605473
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9391
- Wipf, P.¹ Reeves, J.T.² Balachandran, R.³ Giuliano, K.A.⁴ Hamel, E.⁵ Day, B.W.⁶

27
- 0035793878
- (2001) Science , vol.291 , pp. 1766
- Luo, Z.¹ Zhang, Q.² Oderaotoshi, Y.³ Curran, D.P.⁴

28
- 0037041379
- (2002) Tetrahedron Lett. , vol.43 , pp. 2807
- Dobbs, A.¹ McGregor-Johnson, C.²

29
- 0001973110
- Trost, B.M., Fleming, I., Eds.; Pergamon: Oxford
- (1991) Comprehensive Organic Synthesis , vol.6 , pp. 1
- Mitsunobu, O.¹

30
- 0002204826
- Trost, B.M., Fleming, I., Eds.; Pergamon: Oxford
- (1991) Comprehensive Organic Synthesis , vol.6 , pp. 65
- Mitsunobu, O.¹

31
- 0000414496
- (1992) Org. React. (N.Y.) , vol.42 , pp. 335
- Hughes, D.L.¹

32
- 0001640928
- (1996) Org. Prep. Proced. Int. , vol.28 , pp. 127
- Hughes, D.L.¹

33
- 0034606936
- (2000) Tetrahedron Lett. , vol.41 , pp. 797
- Pelletier, J.C.¹ Kincaid, S.²

34
- 0032569908
- (1998) Tetrahedron Lett. , vol.39 , pp. 8751
- Tunoori, A.K.¹ Dutta, D.² Georg, G.I.³

35
- 0000482191
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 3973
- Arnold, L.D.¹ Assil, H.I.² Vederas, J.C.³

36
- 0033546351
- (1999) Tetrahedron Lett. , vol.40 , pp. 4497
- Kiankarimi, M.¹ Lowe, R.² McCarthy, J.R.³ Whitten, J.P.⁴

37
- 0032497352
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2385
- Starkey, G.W.¹ Parlow, J.J.² Flynn, D.L.³

38
- 0032879345
- (1999) Med. Res. Rev. , vol.19 , pp. 408
- Flynn, D.L.¹

39
- 0034699311
- (2000) Org. Lett. , vol.2 , pp. 2999
- Barrett, A.G.M.¹ Roberts, R.S.² Schroder, J.³

40
- 0002667764
- (1981) Synthesis , pp. 1
- Mitsunobu, O.¹

41
- 0000899392
- H. Fenniri. Oxford: Oxford University
- (2001) Combinatorial Chemistry: A Practical Approach , vol.2 , pp. 327
- Curran, D.P.¹ Hadida, S.² Studer, A.³ He, M.⁴ Kim, S.-Y.⁵ Luo, Z.⁶ Larhed, M.⁷ Hallberg, M.⁸ Linclau, B.⁹

42
- 0000925548
- (1987) Synth. Commun. , vol.17 , pp. 409
- Moriarty, R.M.¹ Prakask, I.² Penmasta, R.³

43
- 0030814712
- (1997) Synth. Commun. , vol.27 , pp. 3197
- Starr, J.T.¹ Rai, G.S.² Dang, H.³ McNeils, B.J.⁴

44
- 0032508089
- (1998) Tetrahedron. Lett. , vol.39 , pp. 4405
- Griffin, S.¹ Heath, L.² Wyatt, P.³

45
- 0001019782
- (1989) Tetrahedron Lett. , vol.30 , pp. 5709
- Henry, J.R.¹ Marcin, L.R.² McIntosh, M.C.³ Scola, P.M.⁴ Harris G.D., Jr.⁵ Weinreb, S.M.⁶

46
- 0000595912
- (1981) Tetrahedron Lett. , vol.22 , pp. 3119
- Volante, R.P.¹

47
- 0000287232
- (1986) Tetrahedron Lett. , vol.27 , pp. 5813
- Smith A.B. III¹ Hale, K.J.² Rivero, R.A.³

48
- 0008925991
- 2NHBoc by Procedure A (Table 1, entries 7 and 8).

49
- 0008892243
- Control experiments showed that the FluoroFlash™ cartridges were superior to the homemade silica in terms of loading and separation, and we now routinely use these cartridges for fluorous spe work.

50
- 0008897213
- 2 8, 29.8 min. The derived phospine oxides eluted at 10.6, 22.5, and 28.3 min, respectively.

51
- 0008911056
- 1H NMR spectrum of 21a.

52
- 0008954172
- The results also suggest the precipitation may be at least partly responsible for separation of the hydrophobic fluorous products as well. However, again we know by hplc and other control experiments that the fluorous products are strongly retained under these conditions (see Ref. 25), so the fluorous silica is not just behaving as a filter.

53
- 0008961130
- Fluorous Technologies, Inc., Harmarville, PA, www.fluorous.com.

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