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(g) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
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Ishikawa, T.; Kudo, T.; Shigemori, K.; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633-7637.
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0003527998
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Wiley-VCH: New York
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When 4-hydroxy-2-isoxazoline-2-oxides, prepared through base-promoted reaction of aldehydes bearing a leaving group on the α carbon with activated primary nitroalkanes, were treated with TMS-Cl (1 equiv) and imidazole at room temperature, heterotricyclic compounds were obtained as precursors for linear aminopolyhydroxylated structures; see ref 1c. Tandem inter [4 + 2]/intra [3 + 2] cycloaddition between siloxynitroalkene and chiral vinyl ether was successfully used for the synthesis of cyclic polyhydroxylated amine structures; see ref 1d. For a review, see: Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001; pp 263-274.
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The Nitro Group in Organic Synthesis
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Ono, N.1
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0000851805
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Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, see also the review in ref 3, pp 30-65
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(b) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 321-340; see also the review in ref 3, pp 30-65.
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Comprehensive Organic Synthesis
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Rosini, G.C.O.S.1
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(a) Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372-10373.
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Suzuki, T.2
Itoh, N.3
Tanaka, K.4
Date, T.5
Okamura, K.6
Shibasaki, M.7
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0036495323
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(b) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861-863
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Trost, B.M.1
Yeh, V.S.C.2
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14
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0013083033
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Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin
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(c) For review, see: Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, pp 1075-1090.
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Comprehensive Asymmetric Catalysis
, vol.3
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Shibasaki, M.1
Gröger, H.2
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15
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0242510417
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note
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H-H values; see Supporting Information.
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16
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0002437012
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Larson, G. L., Ed.; Jai Press: Greenwich
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For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996; Vol. 3, pp 1-62. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 57, 7599-7662. See also: (c) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
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(1996)
Advances in Silicon Chemistry
, vol.3
, pp. 1-62
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Tamao, K.1
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17
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0030007621
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For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996; Vol. 3, pp 1-62. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 57, 7599-7662. See also: (c) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
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(1996)
Tetrahedron
, vol.57
, pp. 7599-7662
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Jones, G.R.1
Landais, Y.2
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18
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0000276453
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For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: Greenwich, 1996; Vol. 3, pp 1-62. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 57, 7599-7662. See also: (c) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
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(1983)
Organometallics
, vol.2
, pp. 1694-1696
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Tamao, K.1
Ishida, N.2
Tanaka, T.3
Kumada, M.4
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19
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0242678966
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note
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When chlorodiphenylvinylsilane was employed as a bis-silylating agent, a difficult to separate, multicomponent mixture was furnished as products.
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20
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0242595160
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note
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The relative configuration of minor diastereomer was assigned as 5 by careful analysis of NMR spectra.
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21
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0242678968
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note
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1 substituent in the transition state.
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22
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84985092616
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One promising indirect way of observing the existence of such geometrical isomers of the silyl nitronate is to analyze the products distribution for an appropriate intermolecular cycloaddition reaction. We have not done it yet. Two possible mechanisms deserve consideration for such a geometrical isomerization of the nitronate: one involves a protonation- deprotonation process and the other involves the 1,3-migration of a trimethylsilyl group from one oxygen to another oxygen. For discussion with respect to the 1,3-migration, see: Colvin, E. W.; Beck, A. K.; Bastani, B.; Seebach, D.; Dunitz, J. D. Helv. Chim. Acta 1980, 63, 697-710.
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(1980)
Helv. Chim. Acta
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Colvin, E.W.1
Beck, A.K.2
Bastani, B.3
Seebach, D.4
Dunitz, J.D.5
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23
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0242510418
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note
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No effort has been made to optimize each step of these transformations. It turned out that similar reaction conditions as those employed for 4a or 4b were ineffective for cycloadduct 4c or 4e having a tertiary carbon linking to the nitrogen atom,. We are now making extensive efforts to establish the reaction conditions applicable to the transformation of 4c or 4e to amino polyol derivatives, which will be published elsewhere.
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0001411949
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see also ref 2
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Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 837-838; see also ref 2.
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(1989)
Tetrahedron Lett.
, vol.30
, pp. 837-838
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Saito, S.1
Nakajima, H.2
Inaba, M.3
Moriwake, T.4
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25
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0025362839
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Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; Sarlo, F. D. Tetrahedron Lett. 1990, 31, 3351-3354.
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(1990)
Tetrahedron Lett.
, vol.31
, pp. 3351-3354
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Cicchi, S.1
Goti, A.2
Brandi, A.3
Guarna, A.4
Sarlo, F.D.5
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