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The side product of the reaction (25%) is compound 9a. Figure Presented Conversion of 9a under acidic conditions improved the yield of the desired acetal to 88%.
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The side product of the reaction (25%) is compound 9a. Figure Presented Conversion of 9a under acidic conditions improved the yield of the desired acetal to 88%.
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Prepared from HOCH2CH=CH(CH2)2ODPS
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2ODPS: Nicolaou, K. C.; Lizos, D. E.; Kim, D. W.; Schlawe, D.; Noronha, R. G.; Longbottom, D. A.; Rodriquez, M.; Bucci, M.; Cirino, G. J. Am. Chem. Soc. 2006, 128, 4460-4470.
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It has to be pointed out that, although the RCM reaction was quantitative, attempts to subject compounds 19 and 20 to chromatography in the presence of air resulted in a substantial loss of the material, most probably via oxidation of the diene system. For example, exposure of structurally similar compound A to air gave after 20 min hydroperoxide B in 90% yield. Gromov, A. Ph.D. Thesis in preparation. Figure Presented
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It has to be pointed out that, although the RCM reaction was quantitative, attempts to subject compounds 19 and 20 to chromatography in the presence of air resulted in a substantial loss of the material, most probably via oxidation of the diene system. For example, exposure of structurally similar compound A to air gave after 20 min hydroperoxide B in 90% yield. Gromov, A. Ph.D. Thesis in preparation. Figure Presented
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