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Chemical Communications

Volumn , Issue 23, 2006, Pages 2466-2468

α-Substituted acylsilanes via a highly selective [1,4]-Wittig rearrangement of α-benzyloxyallylsilane

(2) Onyeozili, Edith N a Maleczka Jr , Robert E a

a MICHIGAN STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZYL DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; WITTIG REACTION;

EID: 33745012651 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b603228a Document Type: Article

Times cited : (19)

References (53)

1
- 0001251247
- T. Nakai K. Tomooka Pure Appl. Chem. 1997 69 595 600
- (1997) Pure Appl. Chem. , vol.69 , pp. 595-600
- Nakai, T.¹ Tomooka, K.²

2
- 0000135630
- T. Nakai K. Mikami Org. React. 1994 46 105 209
- (1994) Org. React. , vol.46 , pp. 105-209
- Nakai, T.¹ Mikami, K.²

3
- 0037503118
- Z. Rappoport and M. Ilan, Wiley, London, 749-828 For recent examples see:
- K. Tomooka, in Chemistry of Organolithium Compounds, ed., Z. Rappoport, and, M. Ilan,, Wiley, London, 2004, vol. 2, pp. 749-828
- (2004) Chemistry of Organolithium Compounds, Ed.
- Tomooka In, K.¹

4
- 30144434126
- M. Sasaki M. Higashi H. Masu K. Yamaguchi K. Takeda Org. Lett. 2005 7 5913 5915
- (2005) Org. Lett. , vol.7 , pp. 5913-5915
- Sasaki, M.¹ Higashi, M.² Masu, H.³ Yamaguchi, K.⁴ Takeda, K.⁵

5
- 0037004625
- G. McGowan Aust. J. Chem. 2002 55 799
- (2002) Aust. J. Chem. , vol.55 , pp. 799
- McGowan, G.¹

6
- 0034731542
- J. C. Anderson A. Flaherty M. E. Swarbrick J. Org. Chem. 2000 65 9152 9156
- (2000) J. Org. Chem. , vol.65 , pp. 9152-9156
- Anderson, J.C.¹ Flaherty, A.² Swarbrick, M.E.³

7
- 0035859316
- S. A. Hart C. O. Trindle F. A. Etzkorn Org. Lett. 2001 3 1789 1791
- (2001) Org. Lett. , vol.3 , pp. 1789-1791
- Hart, S.A.¹ Trindle, C.O.² Etzkorn, F.A.³

8
- 0033533643
- R. E. Maleczka, Jr. F. Geng Org. Lett. 1999 1 1111 1113
- (1999) Org. Lett. , vol.1 , pp. 1111-1113
- Maleczka Jr., R.E.¹ Geng, F.²

9
- 0032567292
- P. Antoniotti G. Tonachini J. Org. Chem. 1998 63 9756 9762
- (1998) J. Org. Chem. , vol.63 , pp. 9756-9762
- Antoniotti, P.¹ Tonachini, G.²

10
- 0000654526
- S. E. Gibson P. Ham G. R. Jefferson Chem. Commun. 1998 123 124
- (1998) Chem. Commun. , pp. 123-124
- Gibson, S.E.¹ Ham, P.² Jefferson, G.R.³

11
- 0027142470
- K. Tomooka T. Igarashi T. Nakai Tetrahedron Lett. 1993 34 8139 8142
- (1993) Tetrahedron Lett. , vol.34 , pp. 8139-8142
- Tomooka, K.¹ Igarashi, T.² Nakai, T.³

12
- 0028298610
- K. Tomooka T. Igarashi T. Nakai Tetrahedron 1994 50 5927 5932
- (1994) Tetrahedron , vol.50 , pp. 5927-5932
- Tomooka, K.¹ Igarashi, T.² Nakai, T.³

13
- 0030567340
- K. Tomooka H. Yamamoto T. Nakai J. Am. Chem. Soc. 1996 118 3317 3318
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3317-3318
- Tomooka, K.¹ Yamamoto, H.² Nakai, T.³

14
- 33748819394
- K. Tomooka H. Yamamoto T. Nakai Liebigs Ann. 1997 1275 1281
- (1997) Liebigs Ann. , pp. 1275-1281
- Tomooka, K.¹ Yamamoto, H.² Nakai, T.³

15
- 0033576711
- K. Tomooka H. Yamamoto T. Nakai Angew. Chem., Int. Ed. 1999 38 3741 3743
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 3741-3743
- Tomooka, K.¹ Yamamoto, H.² Nakai, T.³

16
- 0001463708
- S. L. Schreiber M. T. Goulet Tetrahedron Lett. 1987 28 1043 1046
- (1987) Tetrahedron Lett. , vol.28 , pp. 1043-1046
- Schreiber, S.L.¹ Goulet, M.T.²

17
- 0000533321
- E. J. Verner T. Cohen J. Am. Chem. Soc. 1992 114 375 377
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 375-377
- Verner, E.J.¹ Cohen, T.²

18
- 84985641126
- R. Hoffmann R. Brückner Chem. Ber. 1992 125 1957 1963
- (1992) Chem. Ber. , vol.125 , pp. 1957-1963
- Hoffmann, R.¹ Brückner, R.²

19
- 0032569218
- and references cited therein
- R. E. Maleczka, Jr. F. Geng J. Am. Chem. Soc. 1998 120 8551 8552
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8551-8552
- Maleczka Jr., R.E.¹ Geng, F.²

20
- 84981919285
- U. Schöllkopf Angew. Chem., Int. Ed. Engl. 1970 9 763 773
- (1970) Angew. Chem., Int. Ed. Engl. , vol.9 , pp. 763-773
- Schöllkopf, U.¹

21
- 0002049382
- U. Schöllkopf K. Fellenberger M. Rizk Justus Liebigs Ann. Chem. 1970 734 106 115
- (1970) Justus Liebigs Ann. Chem. , vol.734 , pp. 106-115
- Schöllkopf, U.¹ Fellenberger, K.² Rizk, M.³

22
- 0001969076
- and references cited therein
- H. Felkin C. Frajeermann Tetrahedron Lett. 1977 18 3485 3488
- (1977) Tetrahedron Lett. , vol.18 , pp. 3485-3488
- Felkin, H.¹ Frajeermann, C.²

23
- 0003467836
- K. Sayo Y. Kumara T. Nakai Tetrahedron Lett. 1982 23 3931 3934
- (1982) Tetrahedron Lett. , vol.23 , pp. 3931-3934
- Sayo, K.¹ Kumara, Y.² Nakai, T.³

24
- 37049083121
- K. Hayakawa A. Hayashida K. Kanematsu J. Chem. Soc., Chem. Commun. 1988 1108 1110
- (1988) J. Chem. Soc., Chem. Commun. , pp. 1108-1110
- Hayakawa, K.¹ Hayashida, A.² Kanematsu, K.³

25
- 0000733440
- M. Schlösser S. Strunk Tetrahedron 1989 45 2649 2664
- (1989) Tetrahedron , vol.45 , pp. 2649-2664
- Schlösser, M.¹ Strunk, S.²

26
- 0025873262
- W. F. Bailey L. M. Zarcone Tetrahedron Lett. 1991 32 4425 4426
- (1991) Tetrahedron Lett. , vol.32 , pp. 4425-4426
- Bailey, W.F.¹ Zarcone, L.M.²

27
- 84986397386
- W. F. Bailey E. R. Punzalan L. M. Zarcone Heteroat. Chem. 1992 3 55 61
- (1992) Heteroat. Chem. , vol.3 , pp. 55-61
- Bailey, W.F.¹ Punzalan, E.R.² Zarcone, L.M.³

28
- 0034671723
- K. Tomooka H. Yamamoto T. Nakai Angew. Chem., Int. Ed. 2000 39 4500 4502
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4500-4502
- Tomooka, K.¹ Yamamoto, H.² Nakai, T.³

29
- 33745018571
- A. Nakazaki T. Nakai K. Tomooka Angew. Chem., Int. Ed. 2006 45 2235 2238
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2235-2238
- Nakazaki, A.¹ Nakai, T.² Tomooka, K.³

30
- 0033533657
- for the preparation of 1 see: ref. 2d In ref. 6a, we mistakenly assigned 3 as a [2,3]-Wittig derived product. In actuality, this product is the result of a [1,2]-Wittig followed by migration of the TMS group to the β-carbon. If this migration is the result of a direct [1,3]-shift or involves a Brook/vinylogous retro-Brook rearrangement is unclear at this time (also see ref. 5j)
- R. E. Maleczka, Jr. F. Geng Org. Lett. 1999 1 1115 1118
- (1999) Org. Lett. , vol.1 , pp. 1115-1118
- Maleczka Jr., R.E.¹ Geng, F.²

31
- 9444255109
- A. E. Mattson K. A. Scheidt Org. Lett. 2004 6 4363 4366
- (2004) Org. Lett. , vol.6 , pp. 4363-4366
- Mattson, A.E.¹ Scheidt, K.A.²

32
- 1542375011
- A. E. Mattson A. R. Bharadwaj K. A. Scheidt J. Am. Chem. Soc. 2004 126 2314 2315
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 2314-2315
- Mattson, A.E.¹ Bharadwaj, A.R.² Scheidt, K.A.³

33
- 4644246440
- D. A. Nicewicz C. M. Yates J. S. Johnson J. Org. Chem. 2004 69 6548 6555
- (2004) J. Org. Chem. , vol.69 , pp. 6548-6555
- Nicewicz, D.A.¹ Yates, C.M.² Johnson, J.S.³

34
- 0037954633
- X. Linghu D. A. Nicewicz J. S. Johnson Org. Lett. 2002 4 2957 2960
- (2002) Org. Lett. , vol.4 , pp. 2957-2960
- Linghu, X.¹ Nicewicz, D.A.² Johnson, J.S.³

35
- 8744303700
- and references cited therein. For reviews see:
- C. T. Clark B. C. Milgram K. A. Scheidt Org. Lett. 2004 6 3977 3980
- (2004) Org. Lett. , vol.6 , pp. 3977-3980
- Clark, C.T.¹ Milgram, B.C.² Scheidt, K.A.³

36
- 33745018339
- I. Fleming, Pergamon, London, 513-567
- P. C. B. Page and M. J. McKenzie, in Science of Synthesis, ed., I. Fleming,, Pergamon, London, 2002, vol. 4, pp. 513-567
- (2002) Science of Synthesis, Ed.
- Page, P.C.B.¹ McKenzie In, M.J.²

37
- 0001598940
- B. F. Bonini M. C. Franchini M. Fochi Gazz. Chim. Ital. 1997 127 619 628
- (1997) Gazz. Chim. Ital. , vol.127 , pp. 619-628
- Bonini, B.F.¹ Franchini, M.C.² Fochi, M.³

38
- 84944643441
- P. F. Cirillo J. S. Panek Org. Prep. Proced. Int. 1992 24 553 582
- (1992) Org. Prep. Proced. Int. , vol.24 , pp. 553-582
- Cirillo, P.F.¹ Panek, J.S.²

39
- 0346326030
- H. Felkin A. Tambute Tetrahedron Lett. 1969 10 821 822
- (1969) Tetrahedron Lett. , vol.10 , pp. 821-822
- Felkin, H.¹ Tambute, A.²

40
- 1242296131
- N. G. Bhat A. Tamm A. Gorena Synlett 2004 297 298
- (2004) Synlett , pp. 297-298
- Bhat, N.G.¹ Tamm, A.² Gorena, A.³

41
- 10044243727
- Enolate 4 had been trapped previously with allyl bromide to afford α-allyl acylsilane 5 in 15% yield.
- C. Hammaecher I. Ouzzane C. Portella J.-P. Bouillon Tetrahedron 2005 61 657 663
- (2005) Tetrahedron , vol.61 , pp. 657-663
- Hammaecher, C.¹ Ouzzane, I.² Portella, C.³ Bouillon, J.-P.⁴

42
- 33745026650
- Michigan State University, α,β-Unsaturated silylketones have been reported to undergo conjugate additions with cuprates, however no details of these reactions were described in:
- F. Geng, PhD thesis, Michigan State University, 2001
- (2001)
- Geng Phd Thesis, F.¹

43
- 0000423334
- For annulations with allenylsilanes see:
- H. J. Reich M. J. Kelley R. E. Olson R. C. Holtan Tetrahedron 1983 39 949 960
- (1983) Tetrahedron , vol.39 , pp. 949-960
- Reich, H.J.¹ Kelley, M.J.² Olson, R.E.³ Holtan, R.C.⁴

44
- 0000220005
- For cyclopropanations see:
- R. L. Danheiser D. M. Fink Tetrahedron Lett. 1985 26 2513 2516
- (1985) Tetrahedron Lett. , vol.26 , pp. 2513-2516
- Danheiser, R.L.¹ Fink, D.M.²

45
- 0001528673
- For examples of 1,4-additions with TMS-substituted nucleophiles see:
- J. S. Nowick R. L. Danheiser Tetrahedron 1988 44 4113 4134
- (1988) Tetrahedron , vol.44 , pp. 4113-4134
- Nowick, J.S.¹ Danheiser, R.L.²

46
- 0001339951
- A. Ricci A. Degl'Innocenti G. Borselli G. Reginato Tetrahedron Lett. 1987 28 4093 4096
- (1987) Tetrahedron Lett. , vol.28 , pp. 4093-4096
- Ricci, A.¹ Degl'Innocenti, A.² Borselli, G.³ Reginato, G.⁴

47
- 2542439094
- Also see:
- A. Degl'Innocenti P. Ulivi A. Capperucci G. Reginato A. Mordini A. Ricci Synlett 1992 883 886
- (1992) Synlett , pp. 883-886
- Degl'Innocenti, A.¹ Ulivi, P.² Capperucci, A.³ Reginato, G.⁴ Mordini, A.⁵ Ricci, A.⁶

48
- 0033214802
- 2O and brine. Workup was then carried out as described above to afford the α-substituted acylsilane
- I. A. Stergiades M. A. Tius J. Org. Chem. 1999 64 7547 7551
- (1999) J. Org. Chem. , vol.64 , pp. 7547-7551
- Stergiades, I.A.¹ Tius, M.A.²

49
- 33745017844
- NMR and HRMS analysis suggest two molecules of benzaldehyde are incorporated in the product, but the exact structure of this compound is unclear
- NMR and HRMS analysis suggest two molecules of benzaldehyde are incorporated in the product, but the exact structure of this compound is unclear

50
- 16844364568
- The E geometries of the both 12 and 13 were based on the spectral data for 13 being identical to those previously reported for that geometric isomer. See: M. Yamane K. Uera K. Narasaka Bull. Chem. Soc. Jpn. 2005 78 477 486
- (2005) Bull. Chem. Soc. Jpn. , vol.78 , pp. 477-486
- Yamane, M.¹ Uera, K.² Narasaka, K.³

51
- 0037136394
- M. Honda W. Oguchi M. Segi T. Nakajima Tetrahedron 2002 58 6815 6823
- (2002) Tetrahedron , vol.58 , pp. 6815-6823
- Honda, M.¹ Oguchi, W.² Segi, M.³ Nakajima, T.⁴

52
- 27944434660
- S. Itsuno S. Arima N. Haraguchi Tetrahedron 2005 61 12074 12080
- (2005) Tetrahedron , vol.61 , pp. 12074-12080
- Itsuno, S.¹ Arima, S.² Haraguchi, N.³

53
- 33748821472
- I. Fleming J. M. Mwaniki J. Chem. Soc., Perkin Trans. 1 1998 1237 1247
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1237-1247
- Fleming, I.¹ Mwaniki, J.M.²

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