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0001311326
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1 groups located on the same side of the C=C bond). Beslin, P.; Vallée, Y. Tetrahedron 1985, 41, 2691-2705. In contrast, the analogous carbonyl compounds afford trans enolates under similar kinetic conditions.
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Beslin, P.1
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56
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84982480964
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For reported syntheses of α-hydroxydithioesters see: (a) Poupaert, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1976, 85, 431-434. (b) Li, J.; Guha, K.; Creighton, D. J. Biochem. Biophys. Res. Commun. 1991, 181, 657-663. (c) Scheithauer, S. German (East) Patent 86823, 1973.
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Poupaert, J.1
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0026317480
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For reported syntheses of α-hydroxydithioesters see: (a) Poupaert, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1976, 85, 431-434. (b) Li, J.; Guha, K.; Creighton, D. J. Biochem. Biophys. Res. Commun. 1991, 181, 657-663. (c) Scheithauer, S. German (East) Patent 86823, 1973.
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Li, J.1
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58
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84982480964
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German (East) Patent 86823, 1973
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For reported syntheses of α-hydroxydithioesters see: (a) Poupaert, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1976, 85, 431-434. (b) Li, J.; Guha, K.; Creighton, D. J. Biochem. Biophys. Res. Commun. 1991, 181, 657-663. (c) Scheithauer, S. German (East) Patent 86823, 1973.
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Scheithauer, S.1
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59
-
-
4644270477
-
-
note
-
The imine byproduct of the oxidation reaction undergoes hydrolytic cleavage to benzenesulfonamide and the volatile pinacolone.
-
-
-
-
60
-
-
4644346273
-
-
note
-
2 protons (see the Supporting Information).
-
-
-
-
61
-
-
4644260760
-
-
1H NMR data of the pair of (Z) and (E) isomers. The vinylic proton in the (Z) series occurs at approximately δ 6.3 ppm but is substantially deshielded at around 6.8 ppm in the corresponding (E) isomer, (a) Cazes, B.; Huynh, C.; Julia, S.; Ratovelomanana, V.; Ruel, O. J. Chem. Res. (M) 1978, 957-968. (b) Seebach, D.; Bürstinghaus, R.; Gröbel, B.-T.; Kolb, M. Liebigs. Ann. Chem. 1977, 830-845.
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Cazes, B.1
Huynh, C.2
Julia, S.3
Ratovelomanana, V.4
Ruel, O.5
-
62
-
-
84981450407
-
-
1H NMR data of the pair of (Z) and (E) isomers. The vinylic proton in the (Z) series occurs at approximately δ 6.3 ppm but is substantially deshielded at around 6.8 ppm in the corresponding (E) isomer, (a) Cazes, B.; Huynh, C.; Julia, S.; Ratovelomanana, V.; Ruel, O. J. Chem. Res. (M) 1978, 957-968. (b) Seebach, D.; Bürstinghaus, R.; Gröbel, B.-T.; Kolb, M. Liebigs. Ann. Chem. 1977, 830-845.
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Seebach, D.1
Bürstinghaus, R.2
Gröbel, B.-T.3
Kolb, M.4
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63
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0028087642
-
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2. See the Supporting Information. (a) Dannhardt, G.; Kiefer, W. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 509-514. (b) Mazzanti, G.; van Helvoirt, E.; van Vliet, L. A.; Ruinaard, R.; Masiero, S.; Bonini, B. F.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1994, 3299-3304. (c) Schwan, A. L.; Roche, M. R.; Gallagher, J. F.; Ferguson, G. Can. J. Chem. 1994, 72, 312-324.
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Arch. Pharm. (Weinheim, Ger.)
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64
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37049090377
-
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2. See the Supporting Information. (a) Dannhardt, G.; Kiefer, W. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 509-514. (b) Mazzanti, G.; van Helvoirt, E.; van Vliet, L. A.; Ruinaard, R.; Masiero, S.; Bonini, B. F.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1994, 3299-3304. (c) Schwan, A. L.; Roche, M. R.; Gallagher, J. F.; Ferguson, G. Can. J. Chem. 1994, 72, 312-324.
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Mazzanti, G.1
Van Helvoirt, E.2
Van Vliet, L.A.3
Ruinaard, R.4
Masiero, S.5
Bonini, B.F.6
Zwanenburg, B.7
-
65
-
-
0005003154
-
-
2. See the Supporting Information. (a) Dannhardt, G.; Kiefer, W. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 509-514. (b) Mazzanti, G.; van Helvoirt, E.; van Vliet, L. A.; Ruinaard, R.; Masiero, S.; Bonini, B. F.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1994, 3299-3304. (c) Schwan, A. L.; Roche, M. R.; Gallagher, J. F.; Ferguson, G. Can. J. Chem. 1994, 72, 312-324.
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Schwan, A.L.1
Roche, M.R.2
Gallagher, J.F.3
Ferguson, G.4
-
66
-
-
4644331056
-
-
note
-
2O, Claisen rearrangement into a sulfine, and finally rearrangement, via an oxathiirane, with loss of elemental sulfur (see the Supporting Information).
-
-
-
-
67
-
-
4644361254
-
-
note
-
1, which has a phenyl substituent, a 0.7 ppm downfield shift is observed for the vinylic proton, but the singlet for the (Z) isomer again occurs at higher field (δ 7.00 against 7.63 ppm).
-
-
-
-
69
-
-
4644270954
-
-
note
-
The relative configuration was not determined.
-
-
-
-
70
-
-
0000449359
-
-
Sandrinelli, F.; Perrio, S.; Beslin, P. Org. Lett. 1999, 1, 1177-1180.
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Sandrinelli, F.1
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Beslin, P.3
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71
-
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4644373283
-
-
note
-
The yield is calculated from the dithioester based on an optimum value of 50%, as a single equivalent of oxidant is used.
-
-
-
-
74
-
-
0042089066
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(b) Davis, F. A.; Rizvi, S. Q. A.; Ardecky, R.; Gosciniak, D. J.; Friedman, A. J.; Yocklovich, S. G. J. Org. Chem. 1980, 45, 1650-1653.
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Ardecky, R.3
Gosciniak, D.J.4
Friedman, A.J.5
Yocklovich, S.G.6
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