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See also: (b) Tamura, O.; Gotanda, K.; Yoshino, J.; Morita, Y.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Mita, N.; Yamashita, M.; Ishibashi, H.; Sakamoto, M. J. Org. Chem. 2000, 65, 8544-8551.
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Williams, R.M.1
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For a review for nucleophilic additions to nitrones, see: Lombardo, M.; Trombini, C. Synthesis 2000, 759-774. See also: Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326.
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Synthesis
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Trombini, C.2
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0034614462
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For a review for nucleophilic additions to nitrones, see: Lombardo, M.; Trombini, C. Synthesis 2000, 759-774. See also: Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326.
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Tetrahedron
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Trombini, C.2
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For reviews for nucleophilic additions of 2-siloxyfurans, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
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For nucleophilic additions to N-glycosyl nitrones, see: (a) Huber, R.; Knierzinger, A.; Obrecht, J.-P.; Vasella, A. Helv. Chim. Acta 1985, 68, 1730-1747.
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(e) Lantos, I.; Flisak, J.; Liu, L.; Matsuoka, R.; Mendelson, W.; Stevenson, D.; Tubman, K.; Tucker, L.; Zhang, W.-Y.; Adams, J.; Sorenson, M.; Garigipati, R.; Erhardt, K.; Ross, S. J. Org. Chem. 1997, 62, 5385-5391.
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35
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The oxime was prepared by a similar method for dicyclohexylidene congener of 4, see: (a) Iida, H.; Kasahara, K.; Kibayashi, C. J. Am. Chem. Soc. 1986, 108, 4647-4648.
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It is known that addition reaction of N-benzyl congener of 6d with 7 in the presence of TMSOTf gives four stereoisomers of adduct with very low stereoselectivity. The stereoselectivity of the present reaction of 6d, therefore, may be mainly due to the effect of the sugar auxiliary. See: Degiorgis, F.; Lombardo, M.; Trombini, C. Tetrahedon 1997, 53, 11721-11730.
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Trombini, C.3
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0029994555
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7c In the present reaction, DATS giving the major isomer 8 would demand that C(4) carbon of 7 should occupy a very close position to the R group of iminium ion B. However, the reaction of nitrone 6 bearing a bulkier R group gave a higher ratio of 8. Consequently, it seems to be reasonable to assume model E for the formation of 8 instead of DAST.
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Castellari, C.1
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Pietropaolo, G.3
Trombini, C.4
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