-
1
-
-
85037455306
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-
and references therein
-
1. Gorzynski, S. J. Synthesis, 1984, 629-656 and references therein.
-
(1984)
Synthesis
, pp. 629-656
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-
Gorzynski, S.J.1
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2
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-
0028027516
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2. Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 6537-6540.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 6537-6540
-
-
Crotti, P.1
Di Bussolo, V.2
Favero, L.3
Macchia, F.4
Pineschi, M.5
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3
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0030014333
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3. Crotti, P.; Di Bussolo, V.; Favero, L.; Minutolo, F.; Pineschi, M. Tetrahedron: Asymmetry 1996, 7, 1347-1356.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 1347-1356
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-
Crotti, P.1
Di Bussolo, V.2
Favero, L.3
Minutolo, F.4
Pineschi, M.5
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4
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-
0001435803
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-
4. Crotti, P.; Di Bussolo, V.; Favero, L.; Pineschi, M.; Pasero, M. J. Org. Chem. 1996, 07, 9548-9552.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 9548-9552
-
-
Crotti, P.1
Di Bussolo, V.2
Favero, L.3
Pineschi, M.4
Pasero, M.5
-
6
-
-
0000942084
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-
b) Crandall, J. K.; Huntington, R. D.; Brunner, G. L. J. Org. Chem. 1972, 37, 2911-2913.
-
(1972)
J. Org. Chem.
, vol.37
, pp. 2911-2913
-
-
Crandall, J.K.1
Huntington, R.D.2
Brunner, G.L.3
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7
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0013546056
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c) Wolinsky, J.; Hull, P.; White, E M. Tetrahedron 1976, 32, 1335-1338.
-
(1976)
Tetrahedron
, vol.32
, pp. 1335-1338
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-
Wolinsky, J.1
Hull, P.2
White, E.M.3
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8
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0001564641
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For other related procedures, see also: d) Gaoni, Y. Tetrahedron, 1972, 28, 5525-5531.
-
(1972)
Tetrahedron
, vol.28
, pp. 5525-5531
-
-
Gaoni, Y.1
-
11
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0027376442
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6. Dechoux, L.; Ebel, M.; Jung, L.; Stambach, J. F. Tetrahedron Lett. 1993, 34, 7405-7408. In some cases, we were unable to achieve the high yields and results reported in the article (entries 3, 6 and 10, Table)
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 7405-7408
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-
Dechoux, L.1
Ebel, M.2
Jung, L.3
Stambach, J.F.4
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15
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0013538902
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note
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9. The intermediate trans bromohydrins were not separated pure, but directly cyclized to the corresponding epoxides
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-
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17
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0013536254
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note
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4 the geometry of the enolate has no influence on the regio-or stereochemical result of the addition reaction. In the case of 10a,b, the obtainment of 14a,b and 15a,b in the cyclization reaction points to the exclusive formation of the corresponding (Z)-enolate 22a,b (Scheme 3).
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-
-
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18
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0013504724
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note
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12. The epimerization of 12a,b into 13a,b and vice versa under acidic or basic conditions, respectively, can reasonably be rationalized by means of a retro cyclization process through the protonated γ-HK 26a,b and epoxy enol 27a,b (acidic conditions) and alcoholate 28a,b and epoxy enolate 21a,b (basic conditions). The metal chelation between the enolate and the oxirane oxygens favors the cis γ-HK 12a,b under basic conditions. (Formula Presented)
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-
-
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19
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0013507620
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note
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13. It has to be stressed that, in the present study, four-membered cyclic γ-HKs were never formed in these reactions, independently of the type of the starting epoxy ketones and reaction conditions used.
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-
-
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20
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0013540102
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note
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15
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23
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0013468374
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note
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4
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-
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26
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0013504592
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b) Abbas, S. A.; Laurent, A.; Mison, P.; Pellissier, N. Bull. Soc. Chim. Fr. 1986, 288-296.
-
(1986)
Bull. Soc. Chim. Fr.
, pp. 288-296
-
-
Abbas, S.A.1
Laurent, A.2
Mison, P.3
Pellissier, N.4
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28
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0000367622
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d) Paquette, L. A.; Gulday, J. P.; Maynard, G. D. J. Org. Chem. 1989, 54, 5044-5053.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 5044-5053
-
-
Paquette, L.A.1
Gulday, J.P.2
Maynard, G.D.3
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29
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0000359612
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e) Eddaif, A.; Laurent, A.; Mison, P.; Pellissier, N.; Carrupt, P. A.; Vogel, P. J. Org. Chem. 1987, 52, 5548-5560.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 5548-5560
-
-
Eddaif, A.1
Laurent, A.2
Mison, P.3
Pellissier, N.4
Carrupt, P.A.5
Vogel, P.6
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30
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0026763394
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19. a) Yano, K.; Hatta, Y.; Baba, A.; Matsuda, H. Synthesis 1992, 693-696.
-
(1992)
Synthesis
, pp. 693-696
-
-
Yano, K.1
Hatta, Y.2
Baba, A.3
Matsuda, H.4
-
33
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0001403217
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b). Bèguè, J.P.; Bonnet, D.; Charpentier-Morize, M.; Pardo, C. Tetrahedron 1975, 31, 2505-2511.
-
(1975)
Tetrahedron
, vol.31
, pp. 2505-2511
-
-
Bèguè, J.P.1
Bonnet, D.2
Charpentier-Morize, M.3
Pardo, C.4
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