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Jacobsen, E.N.1
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107
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1842457224
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note
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Our catalyst system was applicable to substrates that were functionalized with a C-C double bond or a ketone, without overoxidation. See: refs. [31] and [32].
-
-
-
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108
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1842457227
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note
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The α,β-epoxy peroxy ester 3 is a stable compound that was isolated using common flash column chromatography and can be stored for at least two months at 4°C.
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-
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109
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0043194288
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This catalytic asymmetric epoxidation was applied to the enantioselective syntheses of aeruginosin 298-A and its analogues, see; T. Ohshima, V. Gnanadesikan, T. Shibuguchi, Y. Fukuta, T. Nemoto, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 11206.
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a) T. Nemoto, H. Kakei, V. Gnanadesikan, S.-y. Tosaki, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2002, 124, 14544;
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Nemoto, T.1
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a) R. Martín, P. Romea, T. F. Urpí, J. Vilarrasa, Synlett 1997, 1414;
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Douat, C.1
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118
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1842613844
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note
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For details, see Supporting Information.
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119
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Yoshikoshi, A.4
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121
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1842509444
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note
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2TiCl that functions via single electron transfer proceeded sluggishly.
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-
-
-
122
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1842509446
-
-
note
-
1H NMR analysis.
-
-
-
-
123
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0033515504
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-
2 proceeded incompletely and gave unsatisfactory stereoselectivity (syn:anti 3:7), see: G. E. Keck, C. A. Wager, T. Sell, T. T. Wager, J. Org. Chem. 1999, 64, 2172.
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Keck, G.E.1
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124
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1842613843
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note
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Although diol anti-24a was isolated by preparative thin-layer chromatography, a mixture of diastereomers was used to supply a large amount of substrate for further transformation.
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-
-
-
125
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1842457222
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note
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Enantioselectivity or diastereoselectivity was determined by HPLC analysis.
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126
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0000476716
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M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett. 1984, 25, 2183.
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Roush, W.R.6
Sakai, T.7
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128
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1842457219
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note
-
1H NMR analysis, the ratio of diastereomers was determined to be >95:5.
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-
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129
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1842613842
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note
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McDonald et al. reported a very versatile strategy for syntheses of the 1,3-polyol array without stereochemical limitation and demonstrated stereoselective syntheses of 1,3,5,7-tetraols and 1,3,5,7,9-pentaols. Five of eight possible stereoisomers with several of their enantiomers were synthesized. See Supporting Information for ref. [20]c.
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130
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0032869162
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J. O. Andrianaivoravelona, S. Sahpaz, C. Terreaux, K. Hostettmann, H. Stoecki-Evans, J. Rasolondramanitra, Phytochemistry 1999, 52, 265.
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131
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1842561823
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-
note
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The absolute configuration was determined using Mosher's method. For details, see Supporting Information.
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-
-
-
132
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1842561822
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note
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When acetonide was used as the protecting group, unsatisfactory results were obtained in the following stereoselective ketone reduction (up to β-OH: α-OH 3:1) even after various attempts.
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-
-
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133
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0001489687
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Stereoselective reduction of β-alkoxy ketones, see: ref. [28c]; Y. Mori, A. Takeuchi, H. Kageyama, M. Suzuki, Tetrahedron Lett. 1988, 29, 5423.
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Tetrahedron Lett.
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Mori, Y.1
Takeuchi, A.2
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134
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0032580376
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For representative reviews on ring-closing metathesis, see: a) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413;
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Tetrahedron
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b) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012.
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0001399412
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b) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012.
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137
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L. D. Juliawaty, Y. Watanabe, M. Kitajima, S. A. Achmad, H. Takayama, N. Aimi, Tetrahedron Lett. 2002, 43, 8657, and references therein.
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Juliawaty, L.D.1
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140
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1842457216
-
-
note
-
Enantiomeric excess was determined by HPLC analysis after conversion to the corresponding ketone with benzylmagnesium chloride.
-
-
-
-
141
-
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1842457218
-
-
note
-
Due to the volatility profile of the corresponding ethyl ester of 61, butyl ester was used instead of ethyl ester. When the lithium enolate of the Weinreb amide was used, a slow reaction and moderate conversion were obtained.
-
-
-
-
142
-
-
1842613836
-
-
note
-
Because of the ease of detection by HPLC analysis, benzylidene acetal was used as a protecting group of diol.
-
-
-
-
144
-
-
1842561818
-
-
note
-
There might be an experimental error or an impurity problem.
-
-
-
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145
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0025085919
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M. Fukui, S. Okamoto, T. Sano, T. Nakata, T. Oishi, Chem. Pharm. Bull. 1990, 38, 2890.
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