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For an interesting example of this method applied to synthesize a pyrrolidine, see: b) McGrane, P.L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
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49
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26844494694
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note
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The yield of this reaction is highly dependant on the purity of the vinyl magnesium bromide.
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50
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26844564270
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note
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1,4-dideoxy-1,4-imino-D-ribatol was synthesized from the erythro product 4b via the same methodology. Thus, the stereochemistry of the osmylation is controlled primarily by the oxygen-bearing allylic center and is not influenced by the nitrogen-bearing homoallyic center.
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4444276636
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54
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26844464144
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note
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2 to give 8 as a white solid (1.43g, 82%).
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55
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26844541021
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note
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Carducci, M.; Razavi, H.; Polt, R. Preliminary isotropic refinement: R = 4.5%. The complete structural data for 8 will be published upon complete refinement.
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56
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0025219293
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TEMPO (2,2,6,6-tetramethypiperidinyl-1-oxide) has been shown to be useful in the selective oxidation of 1° alcohols and amino alcohols: a) Siedlecka, R.; Skarzewski, J.; Mlochowski, J. Tetrahedron Lett. 1990, 31, 2177,
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