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0000444658
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Readily obtained on a large scale from β-furylethanol by silylation with TBSC1 (imidazole, DMF, rt) and then DoM (n-BuLi, THF) with DMF as electrophile. See: Kolb, H. C.; Hoffmann, H. M. R. Tetrahedron 1990, 46, 5127.
-
Readily obtained on a large scale from β-furylethanol by silylation with TBSC1 (imidazole, DMF, rt) and then DoM (n-BuLi, THF) with DMF as electrophile. See: Kolb, H. C.; Hoffmann, H. M. R. Tetrahedron 1990, 46, 5127.
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43
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0001890944
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-
For reviews of the use of the Achmatowicz reaction in the synthesis of oxygen-containing heterocycles, see: (a) Georgiadis, M. P.; Albizati, K. F.; Georgiadis, T. M. Org. Prep. Proced. Int. 1992, 24, 95.
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44
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0022902598
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For the initial use of TFA in Kishi reductions, see
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48
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-
37249065926
-
-
To the best of our knowledge, highly diastereoselective reductions of simple pyranones of this type are without precedent. Studies to elucidate the underlying source of the remarkable diastereoselectivity of the Kishi reduction are ongoing and will be reported in due course
-
To the best of our knowledge, highly diastereoselective reductions of simple pyranones of this type are without precedent. Studies to elucidate the underlying source of the remarkable diastereoselectivity of the Kishi reduction are ongoing and will be reported in due course.
-
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49
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0004386928
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(a) Seyferth, D.; Menzel, H.; Dow, A. W.; Flood, T. C. J. Am. Chem. Soc. 1968, 90, 1080.
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51
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34848822791
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-
For a detailed mechanism, see
-
(c) For a detailed mechanism, see: Kühnel, E.; Laffan, D. D. P.; Lloyd-Jones, G. C.; Martínez del Campo, T.; Shepperson, I. R.; Slaughter, J. L. Angew. Chem., Int. Ed. 2007, 46, 7075.
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52
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12344259557
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-
Recent advancements from the Kishi laboratory include the ability to perform this reaction in the presence of chiral sulfonamide ligands. Reported diastereoselectivties for substrates similar to 20 are on the order of 12:1-15:1. See: Namba, K.; Kishi, Y. Org. Lett. 2004, 6, 5031.
-
Recent advancements from the Kishi laboratory include the ability to perform this reaction in the presence of chiral sulfonamide ligands. Reported diastereoselectivties for substrates similar to 20 are on the order of 12:1-15:1. See: Namba, K.; Kishi, Y. Org. Lett. 2004, 6, 5031.
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