-
1
-
-
0038121258
-
-
(a) Fernández de la Pradilla, R.; Castro, S.; Manzano, P.; Priego, J.; Viso, A. J. Org. Chem. 1996, 61, 3586-3587.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 3586-3587
-
-
Fernández De La Pradilla, R.1
Castro, S.2
Manzano, P.3
Priego, J.4
Viso, A.5
-
2
-
-
0037783633
-
-
(b) Fernández de la Pradilla, R.; Castro, S.; Manzano, P.; Martín-Onega, M.; Priego, J.; Viso, A. Rodríguez, A.; Fonseca, I. J. Org. Chem. 1998, 63, 4954-4966.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4954-4966
-
-
Fernández De La Pradilla, R.1
Castro, S.2
Manzano, P.3
Martín-Onega, M.4
Priego, J.5
Rodríguez A, V.A.6
Fonseca, I.7
-
3
-
-
0037111778
-
-
(c) Fernández de la Pradilla, R.; Fernández, J.; Manzano, P.; Méndez, P.; Priego, J.; Tortosa, M.; Viso, A.; Martínez- Ripoll, M.; Rodríguez, A. J. Org. Chem. 2002, 67, 8166-8177.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 8166-8177
-
-
Fernández De La Pradilla, R.1
Fernández, J.2
Manzano, P.3
Méndez, P.4
Priego, J.5
Tortosa, M.6
Viso, A.7
Martínez-Ripoll, M.8
Rodríguez, A.9
-
4
-
-
0000137347
-
-
(d) For the highly selective preparation of spirocyclic bis-sulfinyl oxiranes by a related methodology, see: Aggarwal, V. K.; Barrell, J. K.; Worrall, J. M.; Alexander, R. J. Org. Chem. 1998, 63, 7128-7129.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 7128-7129
-
-
Aggarwal, V.K.1
Barrell, J.K.2
Worrall, J.M.3
Alexander, R.4
-
5
-
-
0036007699
-
-
For a review on the preparation and applications of α-oxy sulfones, including sulfonyl oxiranes, see: (a) Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275-299. For
-
(2002)
J. Chem. Soc., Perkin Trans. 1
, pp. 275-299
-
-
Chemla, F.1
-
6
-
-
85034475814
-
-
other reviews on aspects of the synthesis and reactivity of sulfinyl and sulfonyl oxiranes, see: (b) Satoh, T.; Yamakawa, K. Synlett 1992, 455-468.
-
(1992)
Synlett
, pp. 455-468
-
-
Satoh, T.1
Yamakawa, K.2
-
7
-
-
0001318042
-
-
(c) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
-
(1996)
Chem. Rev.
, vol.96
, pp. 3303-3325
-
-
Satoh, T.1
-
8
-
-
0035861708
-
-
For recent references on applications of sulfinyl and sulfonyl oxiranes, see: (d) Mori, Y.; Hayashi, H. J. Org. Chem. 2001, 66, 8666-8668.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8666-8668
-
-
Mori, Y.1
Hayashi, H.2
-
9
-
-
0037140725
-
-
(e) Satoh, T.; Taguchi, D.; Kurabayashi, A.; Kanoto, M. Tetrahedron 2002, 58, 4217-4224.
-
(2002)
Tetrahedron
, vol.58
, pp. 4217-4224
-
-
Satoh, T.1
Taguchi, D.2
Kurabayashi, A.3
Kanoto, M.4
-
11
-
-
0029814752
-
-
(g) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158-8159.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 8158-8159
-
-
Mori, Y.1
Yaegashi, K.2
Furukawa, H.3
-
12
-
-
0030999573
-
-
(h) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557-4558.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4557-4558
-
-
Mori, Y.1
Yaegashi, K.2
Furukawa, H.3
-
13
-
-
0037430676
-
-
For a recent application of these building blocks within synthetic studies toward yessotoxin and adriatoxin, see: Mori, Y.; Takase, T.; Noyori, R. Tetrahedron Lett. 2003, 44, 2319-2322.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 2319-2322
-
-
Mori, Y.1
Takase, T.2
Noyori, R.3
-
14
-
-
1842739309
-
-
(j) For an application to the synthesis of a fragment of ciguatoxin, see: Inoue, M.; Yamashita, S.; Tatami, A.; Miyazaki, K.; Hirama, M. J. Org. Chem. 2004, 69, 2797-2804.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 2797-2804
-
-
Inoue, M.1
Yamashita, S.2
Tatami, A.3
Miyazaki, K.4
Hirama, M.5
-
15
-
-
24944439529
-
-
(k) For an application to the synthesis of a fragment of gambierol, see: Furuta, H.; Hase, M.; Noyori, R.; Mori, Y. Org. Lett. 2005, 7, 4061-4064.
-
(2005)
Org. Lett.
, vol.7
, pp. 4061-4064
-
-
Mori, Y.1
-
16
-
-
0027278828
-
-
For reviews on the synthesis of carbohydrate derivatives from acyclic precursors, see: (a) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683-5765.
-
(1993)
Tetrahedron
, vol.49
, pp. 5683-5765
-
-
Ager, D.J.1
East, M.B.2
-
18
-
-
0001060027
-
-
(a) Fernández de la Pradilla, R.; Montera, C.; Priego, J.; Martínez-Cruz, L. A. J. Org. Chem. 1998, 63, 9612-9613.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 9612-9613
-
-
Fernández De La Pradilla, R.1
Montera, C.2
Priego, J.3
Martínez-Cruz, L.A.4
-
19
-
-
0141431971
-
-
(b) Fernández de la Pradilla, R.; Manzano, P.; Montera, C.; Priego, J.; Martínez-Ripoll, M.; Martínez-Cruz, L. A. J. Org. Chem. 2003, 68, 7755-7767.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 7755-7767
-
-
Fernández De La Pradilla, R.1
Manzano, P.2
Montera, C.3
Priego, J.4
Martínez-Ripoll, M.5
Martínez-Cruz, L.A.6
-
20
-
-
0024960826
-
-
(a) Adam, W.; Braun, M.; Griesbeck, A.; Lucchini, V.; Staab, E.; Will, B. J. Am. Chem. Soc. 1989, 111, 203-212.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 203-212
-
-
Adam, W.1
Braun, M.2
Griesbeck, A.3
Lucchini, V.4
Staab, E.5
Will, B.6
-
21
-
-
0025785849
-
-
(b) Bailey, M.; Staton, I.; Ashton, P. R.; Markó, I. E.; Ollis, W. D. Tetrahedron: Asymmetry 1991, 2, 495-509.
-
(1991)
Tetrahedron: Asymmetry
, vol.2
, pp. 495-509
-
-
Bailey, M.1
Staton, I.2
Ashton, P.R.3
Markó, I.E.4
Ollis, W.D.5
-
22
-
-
32144444306
-
-
For a preliminary communication, see: Fernández de la Pradilla, R.; Méndez, P.; Priego, J.; Viso, A. J. Chem. Soc., Perkin Trans. 1 1999, 1247-1249.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 1247-1249
-
-
Fernández De La Pradilla, R.1
Méndez, P.2
Priego, J.3
Viso, A.4
-
24
-
-
49249151283
-
-
(b) Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 20, 4733-4736.
-
(1979)
Tetrahedron Lett.
, vol.20
, pp. 4733-4736
-
-
Rossiter, B.E.1
Verhoeven, T.R.2
Sharpless, K.B.3
-
26
-
-
0342881496
-
-
Itoh, T.; Jitsukawa, K.; Kaneda, K.; Teranishi, S. J. Am. Chem. Soc. 1979, 101, 159-169.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 159-169
-
-
Itoh, T.1
Jitsukawa, K.2
Kaneda, K.3
Teranishi, S.4
-
27
-
-
37049081864
-
-
Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1995, 141-148.
-
(1995)
J. Chem. Soc., Perkin Trans. 1
, pp. 141-148
-
-
Jackson, R.F.W.1
Standen, S.P.2
Clegg, W.3
McCamley, A.4
-
28
-
-
0041757975
-
-
For an excellent review on sulfonyl 1,3-dienes, see: Bäckvall, J.-E.; Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 1998, 98, 2291-2312.
-
(1998)
Chem. Rev.
, vol.98
, pp. 2291-2312
-
-
Bäckvall, J.-E.1
Chinchilla, R.2
Nájera, C.3
Yus, M.4
-
29
-
-
0002656496
-
-
For reports somewhat complimentary to our own results, see: (a) Urones, J. G.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Bastida, A. J.; San Feliciano, S. G.; Díez, D.; Goodman, J. M. Synlett 1998, 1361-1363.
-
(1998)
Synlett
, pp. 1361-1363
-
-
Urones, J.G.1
Marcos, I.S.2
Garrido, N.M.3
Basabe, P.4
Bastida, A.J.5
San Feliciano, S.G.6
Díez, D.7
Goodman, J.M.8
-
30
-
-
0001118918
-
-
(b) Urones, J. G.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; San Feliciano, S. G.; Coca, R.; Díez, D. Synlett 1998, 1364-1365.
-
(1998)
Synlett
, pp. 1364-1365
-
-
Urones, J.G.1
Marcos, I.S.2
Garrido, N.M.3
Basabe, P.4
San Feliciano, S.G.5
Coca, R.6
Díez, D.7
-
31
-
-
0030927441
-
-
See references cited in: Adam, W.; Corma, A.; Reddy, T. I.; Renz, M. J. Org. Chem. 1997, 62, 3631-3637.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 3631-3637
-
-
Adam, W.1
Corma, A.2
Reddy, T.I.3
Renz, M.4
-
32
-
-
33644550453
-
-
note
-
At long reaction times, other products, not fully identified, presumably derived from overoxidation were obtained.
-
-
-
-
33
-
-
0023626842
-
-
3, Dess-Martin, etc. (a) Corey, E. J.; Su, W.-G. J. Am. Chem. Soc. 1987, 109, 7534-7536.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 7534-7536
-
-
Corey, E.J.1
Su, W.-G.2
-
34
-
-
0001209483
-
-
(b) Morikawa, T.; Nishiwaki, T.; Iitaka, Y.; Kobayashi, Y. Tetrahedron Lett. 1987, 28, 671-674.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 671-674
-
-
Morikawa, T.1
Nishiwaki, T.2
Iitaka, Y.3
Kobayashi, Y.4
-
35
-
-
37049085344
-
-
(c) Valverde, S.; García-Ochoa, S.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 1714-1715.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 1714-1715
-
-
Valverde, S.1
García-Ochoa, S.2
Martín-Lomas, M.3
-
36
-
-
0023838949
-
-
(d) Corey, E. J.; Kang, M.-C.; Desai, M. C.; Ghosh, A. K.; Houpis, I. N. J. Am. Chem. Soc. 1988, 110, 649-651.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 649-651
-
-
Corey, E.J.1
Kang, M.-C.2
Desai, M.C.3
Ghosh, A.K.4
Houpis, I.N.5
-
38
-
-
33845278599
-
-
(b) Brückner, C.; Holzinger, H.; Reissig, H.-U. J. Org. Chem. 1988, 52, 2450-2456.
-
(1988)
J. Org. Chem.
, vol.52
, pp. 2450-2456
-
-
Brückner, C.1
Holzinger, H.2
Reissig, H.-U.3
-
41
-
-
8344223214
-
-
(a) Kozikowski, A. P.; Sorgi, K. L.; Wang, B. C. Xu, Z. Tetrahedron Lett. 1983, 24, 1563-1566.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 1563-1566
-
-
Kozikowski, A.P.1
Sorgi, K.L.2
Wang, B.C.3
Xu, Z.4
-
43
-
-
0033616106
-
-
For recent developments in this field, see: (c) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208-12209.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 12208-12209
-
-
Larsen, C.H.1
Ridgway, B.H.2
Shaw, J.T.3
Woerpel, K.A.4
-
45
-
-
0001072616
-
-
Interestingly, hindered isopropylidenedioxy ribose acetates are allylated under similar conditions, see: Wilcox, C. S.; Otoski, R. M. Tetrahedron Lett. 1986, 27, 1011-1014.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 1011-1014
-
-
Wilcox, C.S.1
Otoski, R.M.2
-
46
-
-
0001210758
-
-
(a) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-4731.
-
(1986)
J. Org. Chem.
, vol.51
, pp. 4728-4731
-
-
Takeda, Y.1
Matsumoto, T.2
Sato, F.3
-
47
-
-
0001061154
-
-
(b) Howe, G. P.; Wang, S.; Procter, G. Tetrahedron Lett. 1987, 28, 2629-2632.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 2629-2632
-
-
Howe, G.P.1
Wang, S.2
Procter, G.3
-
48
-
-
0026625829
-
-
(c) Wang, S.; Howe, G. P.; Mahal, R. S.; Procter, G. Tetrahedron Lett. 1992, 33, 3351-3354.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 3351-3354
-
-
Wang, S.1
Howe, G.P.2
Mahal, R.S.3
Procter, G.4
-
49
-
-
0021775497
-
-
(d) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30.
-
(1985)
Angew. Chem., Int. Ed. Engl.
, vol.24
, pp. 1-30
-
-
Masamune, S.1
Choy, W.2
Petersen, J.S.3
Sita, L.R.4
-
50
-
-
33751499016
-
-
(e) For a leading reference on reagent controlled allylation of α,β-epoxy aldehydes, see: Roush, W. R.; Straub, J. A.; VanNieuwenhze, M. S. J. Org. Chem. 1991, 56, 1636-1648.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 1636-1648
-
-
Roush, W.R.1
Straub, J.A.2
Vannieuwenhze, M.S.3
-
51
-
-
0032192220
-
-
(f) See also: Williams, D. R.; Brooks, D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251-7254.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 7251-7254
-
-
Williams, D.R.1
Brooks, D.A.2
Meyer, K.G.3
Clark, M.P.4
-
52
-
-
33644560137
-
-
note
-
The stereochemistry of the new chiral center is assigned tentatively in analogy with the results of Procter for nucleophilic additions to α,β-epoxy aldehydes. See ref 17b.
-
-
-
-
53
-
-
0032811141
-
-
For leading references on sulfonyl participation in chelated intermediates, see: (a) Yakura, T.; Tanaka, K.; Iwamoto, M.; Nameki, M.; Ikeda, M. Synlett 1999, 1313-1315.
-
(1999)
Synlett
, pp. 1313-1315
-
-
Yakura, T.1
Tanaka, K.2
Iwamoto, M.3
Nameki, M.4
Ikeda, M.5
-
54
-
-
0001373323
-
-
(b) Marcantoni, E.; Cingolani, S.; Bartoli, G.; Bosco, M.; Sambri, L. J. Org. Chem. 1998, 63, 3624-3630.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 3624-3630
-
-
Marcantoni, E.1
Cingolani, S.2
Bartoli, G.3
Bosco, M.4
Sambri, L.5
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