-
3
-
-
0028926606
-
-
(c) Chong, J. M.; Clarke, I. S.; Koch, I.; Olbach, P. C.; Taylor, N. J. Tetrahedron: Asymmetry 1995, 6, 409.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 409
-
-
Chong, J.M.1
Clarke, I.S.2
Koch, I.3
Olbach, P.C.4
Taylor, N.J.5
-
5
-
-
0344382102
-
-
(a) Otten, S.; Fröhlich, R.; Hanfe, G. Tetrahedron: Asymmetry 1998, 9, 189.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 189
-
-
Otten, S.1
Fröhlich, R.2
Hanfe, G.3
-
6
-
-
0000421034
-
-
(b) Julienne, K.; Metzner, P.; Henryon, V.; Greiner, A. J. Org. Chem. 1998, 63, 4532.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4532
-
-
Julienne, K.1
Metzner, P.2
Henryon, V.3
Greiner, A.4
-
7
-
-
0025886768
-
-
(a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
-
(1991)
Tetrahedron: Asymmetry
, vol.2
, pp. 569
-
-
Burk, M.J.1
Feaster, J.E.2
Harlow, R.L.3
-
8
-
-
0000585749
-
-
and references cited therein
-
(b) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423; and references cited therein.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 4423
-
-
Burk, M.J.1
Harper, T.G.P.2
Kalberg, C.S.3
-
9
-
-
0030058555
-
-
(c) Wiesaner, C.; Kratky, C.; Weissensteiner, W. Tetrahedron: Asymmetry 1996, 7, 397.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 397
-
-
Wiesaner, C.1
Kratky, C.2
Weissensteiner, W.3
-
10
-
-
0037069705
-
-
(a) Amador, M.; Ariza, X.; Garcia, J.; Sevilla, S. Org. Lett. 2002, 4, 4511.
-
(2002)
Org. Lett.
, vol.4
, pp. 4511
-
-
Amador, M.1
Ariza, X.2
Garcia, J.3
Sevilla, S.4
-
11
-
-
0035136250
-
-
(b) Ariza, X.; Garcia, J.; López, M.; Montserrat, L. Synlett 2001, 120.
-
(2001)
Synlett
, pp. 120
-
-
Ariza, X.1
Garcia, J.2
López, M.3
Montserrat, L.4
-
12
-
-
33746442416
-
-
(5) For an overview on the desymmetrization of meso and other prochiral compounds in asymmetric synthesis, see: (a) Willis, M. C. J. Chem. Soc., Perkin Trans, 1 1999, 1765. (b) Magnunson, S. R. Tetrahedron 1995, 51, 2167. (c) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
-
(1999)
J. Chem. Soc., Perkin Trans, 1
, pp. 1765
-
-
Willis, M.C.1
-
13
-
-
0028799792
-
-
For an overview on the desymmetrization of meso and other prochiral compounds in asymmetric synthesis, see: (a) Willis, M. C. J. Chem. Soc., Perkin Trans, 1 1999, 1765. (b) Magnunson, S. R. Tetrahedron 1995, 51, 2167. (c) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
-
(1995)
Tetrahedron
, vol.51
, pp. 2167
-
-
Magnunson, S.R.1
-
14
-
-
0000458209
-
-
For an overview on the desymmetrization of meso and other prochiral compounds in asymmetric synthesis, see: (a) Willis, M. C. J. Chem. Soc., Perkin Trans, 1 1999, 1765. (b) Magnunson, S. R. Tetrahedron 1995, 51, 2167. (c) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
-
(1993)
Chem. Rev.
, vol.93
, pp. 1307
-
-
Hoveyda, A.H.1
Evans, D.A.2
Fu, G.C.3
-
15
-
-
0023897844
-
-
Park, B. K.; Nakagawa, M.; Hirota, A.; Nakayama, M. J. Antibiot. 1988, 41, 751.
-
(1988)
J. Antibiot.
, vol.41
, pp. 751
-
-
Park, B.K.1
Nakagawa, M.2
Hirota, A.3
Nakayama, M.4
-
17
-
-
0030865419
-
-
(b) Ghatak, A.; Sarkar, S.; Ghosh, S. Tetrahedron 1997, 53, 17335.
-
(1997)
Tetrahedron
, vol.53
, pp. 17335
-
-
Ghatak, A.1
Sarkar, S.2
Ghosh, S.3
-
18
-
-
0032080815
-
-
(c) Mandal, P. K.; Maiti, G.; Roy, S. C. J. Org. Chem. 1998, 63, 2829.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2829
-
-
Mandal, P.K.1
Maiti, G.2
Roy, S.C.3
-
24
-
-
0035973760
-
-
(e) Kongsaeree, P.; Meepowpan, P.; Thebtaranonth, Y. Tetrahedron: Asymmetry 2001, 12, 1913.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 1913
-
-
Kongsaeree, P.1
Meepowpan, P.2
Thebtaranonth, Y.3
-
25
-
-
0026782629
-
-
(a) de Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 4567
-
-
De Azevedo, M.B.M.1
Murta, M.M.2
Greene, A.E.3
-
26
-
-
0027465071
-
-
(b) Murta, M. M.; de Azevedo, M. B. M.; Greene, A. E. Synth. Commun. 1993, 23, 495.
-
(1993)
Synth. Commun.
, vol.23
, pp. 495
-
-
Murta, M.M.1
De Azevedo, M.B.M.2
Greene, A.E.3
-
28
-
-
0029165982
-
-
(b) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 5628
-
-
Takahata, H.1
Uchida, Y.2
Momose, T.3
-
29
-
-
0029977883
-
-
(c) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G. Chem. Commun. 1996, 1289.
-
(1996)
Chem. Commun.
, pp. 1289
-
-
Drioli, S.1
Felluga, F.2
Forzato, C.3
Nitti, P.4
Pitacco, G.5
-
32
-
-
0033603429
-
-
(f) Masaki, Y.; Arasaki, H.; Itoh, A. Tetrahedron Lett. 1999, 40, 4829.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 4829
-
-
Masaki, Y.1
Arasaki, H.2
Itoh, A.3
-
33
-
-
0037415070
-
-
(g) Chhor, R. B.; Nosse, B.; Sörgel, S.; Böhm, C.; Seitz, M.; Reiser, O. Chem.-Eur. J. 2003, 9, 260.
-
(2003)
Chem.-Eur. J.
, vol.9
, pp. 260
-
-
Chhor, R.B.1
Nosse, B.2
Sörgel, S.3
Böhm, C.4
Seitz, M.5
Reiser, O.6
-
34
-
-
0032480917
-
-
(11) In this connection it should be pointed out that the reduction of related alk-2-ene-1,4-diones gives lower stereoselectivities: (a) Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. Tetrahedron 1998, 54, 14947. (b) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Manzanal, J.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1091.
-
(1998)
Tetrahedron
, vol.54
, pp. 14947
-
-
Bach, J.1
Berenguer, R.2
Garcia, J.3
López, M.4
Manzanal, J.5
Vilarrasa, J.6
-
35
-
-
0031562081
-
-
In this connection it should be pointed out that the reduction of related alk-2-ene-1,4-diones gives lower stereoselectivities: (a) Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. Tetrahedron 1998, 54, 14947. (b) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Manzanal, J.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1091.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 1091
-
-
Bach, J.1
Berenguer, R.2
Garcia, J.3
Loscertales, T.4
Manzanal, J.5
Vilarrasa, J.6
-
38
-
-
0037041356
-
-
(a) Amador, M.; Ariza, X.; Garcia, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 2691
-
-
Amador, M.1
Ariza, X.2
Garcia, J.3
Ortiz, J.4
-
39
-
-
0037037959
-
-
(b) Diez, R. S.; Adger, B.; Carreira, E. M. Tetrahedron 2002, 58, 8341.
-
(2002)
Tetrahedron
, vol.58
, pp. 8341
-
-
Diez, R.S.1
Adger, B.2
Carreira, E.M.3
-
40
-
-
0035052373
-
-
An attempt to obtain (S,S)-5 by double addition of acetylene to hexanal under similar conditions also failed, see: Sasaki, H.; Boyall, D.; Carreira, E. M. Helv. Chim. Acta 2001, 84, 964.
-
(2001)
Helv. Chim. Acta
, vol.84
, pp. 964
-
-
Sasaki, H.1
Boyall, D.2
Carreira, E.M.3
-
41
-
-
0035802344
-
-
(a) In this case the main process seems to be the concomitant aldehyde aldol self-condensation: Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9687
-
-
Anand, N.K.1
Carreira, E.M.2
-
42
-
-
0038252959
-
-
(b) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373.
-
(2000)
Acc. Chem. Res.
, vol.33
, pp. 373
-
-
Frantz, D.E.1
Fässler, R.2
Tomooka, C.S.3
Carreira, E.M.4
-
45
-
-
0000016656
-
-
(a) Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 7570
-
-
Xu, D.1
Crispino, G.A.2
Sharpless, K.B.3
-
46
-
-
4444276636
-
-
(b) For a review on catalytic asymmetric dihydroxylation, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
-
(1994)
Chem. Rev.
, vol.94
, pp. 2483
-
-
Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
-
47
-
-
0003441482
-
-
Wiley: New York
-
(19) For some reviews on allylic rearrangements catalyzed by Pd(II), see: (a) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: New York, 1995, 399. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579.
-
(1995)
Palladium Reagents and Catalysts. Innovations in Organic Synthesis
, pp. 399
-
-
Tsuji, J.1
-
48
-
-
84985634168
-
-
For some reviews on allylic rearrangements catalyzed by Pd(II), see: (a) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: New York, 1995, 399. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579.
-
(1984)
Angew. Chem., Int. Ed. Engl.
, vol.23
, pp. 579
-
-
Overman, L.E.1
-
49
-
-
0347388095
-
-
note
-
19F NMR and HPLC), we assumed that its optical purity should be ≥98% ee on the basis of that found for (S,S)-3. Absolute configuration of diol 3 revealed it to be identical to that obtained from reduction of diketone 5.
-
-
-
-
52
-
-
0034826477
-
-
(22) For recent stereoselective applications, see: (a) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 2001, 123, 3687. (b) Saito, S.; Kuroda, A.; Matsunaga, H.; Ikeda, S. Tetrahedron 1996, 52, 13919.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 3687
-
-
Trost, B.M.1
Lee, C.B.2
-
53
-
-
0030605047
-
-
For recent stereoselective applications, see: (a) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 2001, 123, 3687. (b) Saito, S.; Kuroda, A.; Matsunaga, H.; Ikeda, S. Tetrahedron 1996, 52, 13919.
-
(1996)
Tetrahedron
, vol.52
, pp. 13919
-
-
Saito, S.1
Kuroda, A.2
Matsunaga, H.3
Ikeda, S.4
-
54
-
-
0001377606
-
-
Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart
-
For a detailed review on [3,3]-sigmatropic rearrangements, see: Frauenrath, H. In Houben-Weyl, Methods of Organic Chemistry, Vol. E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995, 3301.
-
(1995)
Houben-Weyl, Methods of Organic Chemistry
, vol.E21
, pp. 3301
-
-
Frauenrath, H.1
-
56
-
-
0037041597
-
-
(b) Chai, Y.; Hong, S.-P.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. Tetrahedron 2002, 58, 2905.
-
(2002)
Tetrahedron
, vol.58
, pp. 2905
-
-
Chai, Y.1
Hong, S.-P.2
Lindsay, H.A.3
McFarland, C.4
McIntosh, M.C.5
-
57
-
-
2542433188
-
-
Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 3936
-
-
Carlsen, P.H.J.1
Katsuki, T.2
Martin, V.S.3
Sharpless, K.B.4
-
58
-
-
0346267223
-
-
Mathre, J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A. ; Mohan, J. J.; Jones, E. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. Org. Chem. 1991, 56, 751.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 751
-
-
Mathre, J.1
Jones, T.K.2
Xavier, L.C.3
Blacklock, T.J.4
Reamer, R.A.5
Mohan, J.J.6
Jones, E.T.7
Hoogsteen, K.8
Baum, M.W.9
Grabowski, E.J.10
-
59
-
-
0000846718
-
-
Bach, J.; Berenguer, R.; Garcia, J.; López, M.; Manzanal, J.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 9021
-
-
Bach, J.1
Berenguer, R.2
Garcia, J.3
López, M.4
Manzanal, J.5
Vilarrasa, J.6
-
60
-
-
0017337980
-
-
Bicking, J. B.; Robb, C. M.; Smith, R. L.; Cragoe, E. J. Jr.; Kuehl, F. A. Jr.; Mandel, L. R. J. Med. Chem. 1977, 20, 35.
-
(1977)
J. Med. Chem.
, vol.20
, pp. 35
-
-
Bicking, J.B.1
Robb, C.M.2
Smith, R.L.3
Cragoe Jr., E.J.4
Kuehl Jr., F.A.5
Mandel, L.R.6
-
61
-
-
51249163551
-
-
Knothe, G.; Bagby, M. O.; Weisleder, D. J. Am. Oil Chem. Soc. 1995, 72, 1021.
-
(1995)
J. Am. Oil Chem. Soc.
, vol.72
, pp. 1021
-
-
Knothe, G.1
Bagby, M.O.2
Weisleder, D.3
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