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78049489875
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The yields shown for the second and third steps in Scheme 2 result from optimization performed after the publication of ref 11. Ph.D. Dissertation, Monash University, Clayton, Victoria, Australia
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Bromfield, K.M.1
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78049492642
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A preliminary report (11) describes a reaction similar to the one that produced 5a from the crotonate 1a, but in the previous study, the experiment was performed with the corresponding ethyl ester. While the dr's obtained with the ethyl and tert -butyl esters were very similar, the yield was much lower for the ethyl ester (39%), presumably as a result of competing 1,2-addition of the lithium amide 2. The use of the bulkier tert -butyl ester is known to limit this undesired side reaction. (10)
-
A preliminary report (11) describes a reaction similar to the one that produced 5a from the crotonate 1a, but in the previous study, the experiment was performed with the corresponding ethyl ester. While the dr's obtained with the ethyl and tert -butyl esters were very similar, the yield was much lower for the ethyl ester (39%), presumably as a result of competing 1,2-addition of the lithium amide 2. The use of the bulkier tert -butyl ester is known to limit this undesired side reaction. (10)
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15044347792
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41549104832
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78049487945
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19th International Symposium on Fluorine Chemistry, Jackson Hole, WY,; Abstract 160, p
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33746456336
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In this case, the yield of the conjugate addition reaction is compromised by isomerization of the double bond
-
In this case, the yield of the conjugate addition reaction is compromised by isomerization of the double bond: Davies, S. G.; Garrido, N. M.; Kruchinin, D.; Ichihara, O.; Kotchie, L. J.; Price, P. D.; Price Mortimer, A. J.; Russell, A. J.; Smith, A. D. Tetrahedron: Asymmetry 2006, 17, 1793
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