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Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
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81
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-
64249170846
-
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The enantiomeric excess was determined to be 98% for both 15a and ent-15a as observed with Chiralcel OD 99/1 (hexanes/IPA) at 1 mL/min (tR 35:92 for 15a and 45:17 for ent-15a).
-
The enantiomeric excess was determined to be 98% for both 15a and ent-15a as observed with Chiralcel OD 99/1 (hexanes/IPA) at 1 mL/min (tR 35:92 for 15a and 45:17 for ent-15a).
-
-
-
-
82
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0028909387
-
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For preparation of (2R,3R)-3-(triphenylsilyl)-2,3- epoxypropane-1-ol see: Raubo, P.; Wicha, J. Tetrahedron: Asymmetry 1995, 6, 577.
-
For preparation of (2R,3R)-3-(triphenylsilyl)-2,3- epoxypropane-1-ol see: Raubo, P.; Wicha, J. Tetrahedron: Asymmetry 1995, 6, 577.
-
-
-
-
83
-
-
84869275616
-
-
Elevated temperatures (-20, 0, and 25°C) under the described conditions for the (E)-vinylsilane did not provide the desired epoxide.
-
Elevated temperatures (-20, 0, and 25°C) under the described conditions for the (E)-vinylsilane did not provide the desired epoxide.
-
-
-
-
84
-
-
64249127149
-
-
A Shi epoxidation of 16 was also considered; however, literature precedent showed attenuated ee values for similar systems, see ref 32d for more information
-
A Shi epoxidation of 16 was also considered; however, literature precedent showed attenuated ee values for similar systems, see ref 32d for more information.
-
-
-
-
85
-
-
64249138143
-
-
Lipase AK Amano 20, Lipase PS Amano, and Lipase PS-D Amano were initially screened. Lipase PS-D was found to be superior.
-
Lipase AK "Amano" 20, Lipase PS "Amano", and Lipase PS-D "Amano" were initially screened. Lipase PS-D was found to be superior.
-
-
-
-
86
-
-
84869265542
-
-
R 5:03 for 15b and 7.08 for ent-15b).
-
R 5:03 for 15b and 7.08 for ent-15b).
-
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87
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2542433188
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Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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Carlsen, P.H.J.1
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-
88
-
-
64249095551
-
-
Decomposition of cis and trans epoxide acids was noticed upon prolonged storage or column chromatography.
-
Decomposition of cis and trans epoxide acids was noticed upon prolonged storage or column chromatography.
-
-
-
-
89
-
-
64249098618
-
-
During the course of oxidation, the reaction solution became a dark green color with a black suspension, suggesting an inactive catalytic system. To drive the reaction to completion, catalyst loading was increased and extended reaction times were explored with little success. Only a reset of the catalytic system provided full conversion
-
During the course of oxidation, the reaction solution became a dark green color with a black suspension, suggesting an inactive catalytic system. To drive the reaction to completion, catalyst loading was increased and extended reaction times were explored with little success. Only a reset of the catalytic system provided full conversion.
-
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90
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0000860380
-
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Hudrlik, P. F.; Ma, D.; Bhamidipati, R. S.; Hurdlik, A. M. J. Org. Chem. 1996, 61, 8655.
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(a) Davis, A. P.; Hughes, G. J.; Lowndes, P. R.; Robbins, C. M.; Thomas, E. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1981, 1, 1934.
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Whitham, G.H.6
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95
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Siriwardane, U.; Chu, S. S. C.; Buynak, J. D. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1989, C45, 531.
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Siriwardane, U.1
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99
-
-
2742569677
-
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It has been suggested that silicon prefers an axial orientation for both electronic and steric reasons but may still eliminate even without optimal orbital overlap. For a detailed discussion and relevant examples see: Lambert, J. B. Tetrahedron 1990, 46, 2677
-
It has been suggested that silicon prefers an axial orientation for both electronic and steric reasons but may still eliminate even without optimal orbital overlap. For a detailed discussion and relevant examples see: Lambert, J. B. Tetrahedron 1990, 46, 2677.
-
-
-
-
100
-
-
0030914643
-
-
Intramolecular silyl-modified Sakurai condensations of vinylsilanes suggest allylic strain plays a role in stereochemical outcome: Marko, I. E, Dobbs, A. P, Seheirmann, V. Chellé, F, Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899
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Intramolecular silyl-modified Sakurai condensations of vinylsilanes suggest allylic strain plays a role in stereochemical outcome: Marko, I. E.; Dobbs, A. P.; Seheirmann, V. Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899.
-
-
-
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101
-
-
0034966749
-
-
It is conceivable that an aronia-Cope rearrangement could play a role in the stereochemical outcome of these reactions; however, no byproducts from this pathway were observed. For an example of oxonia-Cope rearrangements in allyl systems, see: Roush, W. R.; Dilley, G. J. Synlett 2001, 955.
-
It is conceivable that an aronia-Cope rearrangement could play a role in the stereochemical outcome of these reactions; however, no byproducts from this pathway were observed. For an example of oxonia-Cope rearrangements in allyl systems, see: Roush, W. R.; Dilley, G. J. Synlett 2001, 955.
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102
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(a) Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. 1965, 4, 1075.
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64249153570
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The homoallylic substrates were converted to 1,1-dimethyl acetonides in a three-step sequence
-
The homoallylic substrates were converted to 1,1-dimethyl acetonides in a three-step sequence.
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109
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and references found therein
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0037034362
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For a previous example of spirocvclization in the presence of DDQ see
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116
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64249114450
-
-
Anhydrous conditions resulted in no reactions while using phosphate buffer (pH 7) provided 19% yield of the desired spirocycle.
-
Anhydrous conditions resulted in no reactions while using phosphate buffer (pH 7) provided 19% yield of the desired spirocycle.
-
-
-
-
117
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-
64249158653
-
-
Conditions found in Table 3 were also applied to 44 with little success.
-
Conditions found in Table 3 were also applied to 44 with little success.
-
-
-
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120
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64249155061
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2) in the DDQ oxidation of silyl enol ethers has also been noted, see: (a) Fleming, I.; Paterson, I. Synthesis 1979, 736.
-
2) in the DDQ oxidation of silyl enol ethers has also been noted, see: (a) Fleming, I.; Paterson, I. Synthesis 1979, 736.
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64249172173
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The unknown product was obtained as a mixture of isomers with a loss of C2-C3 olefin. We were unable to separate the mixture for characterization.
-
The unknown product was obtained as a mixture of isomers with a loss of C2-C3 olefin. We were unable to separate the mixture for characterization.
-
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135
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