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84929366528
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The lower Z / E selectivity results from slow catalyst initiation to form compound 3 and generates a small amount of a Co-H leading to the (E) isomer. The position of the deuterium in the (E)-vinylboronate ester product implies that the (E) isomer resulted from a Co-H rather than the isomerization of 5-Pro-(Z) to 5 - Pro-(E).
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The lower Z / E selectivity results from slow catalyst initiation to form compound 3 and generates a small amount of a Co-H leading to the (E) isomer. The position of the deuterium in the (E)-vinylboronate ester product implies that the (E) isomer resulted from a Co-H rather than the isomerization of 5-Pro-(Z) to 5-Pro-(E).
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50
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The 85:15 ratio was determined from the 1H NMR spectrum of the benzene- d 6 solution of the isomers of 5. Upon quenching with DCl, the (Z):(E) ratio of the resulting organic product was measured by GC (the small GC response factor variations in the (Z) and (E) vinylboronate esters were not corrected) to be 80:20. Analyzing the organic product by quantitative 13C NMR spectroscopy revealed a 75:25 ratio. We believe that this slight discrepancy in the isomeric ratio is not due to isomerization but rather due to the use of different analytical methods to determine the ratio.
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The 85:15 ratio was determined from the 1H NMR spectrum of the benzene- d 6 solution of the isomers of 5. Upon quenching with DCl, the (Z):(E) ratio of the resulting organic product was measured by GC (the small GC response factor variations in the (Z) and (E) vinylboronate esters were not corrected) to be 80:20. Analyzing the organic product by quantitative 13C NMR spectroscopy revealed a 75:25 ratio. We believe that this slight discrepancy in the isomeric ratio is not due to isomerization but rather due to the use of different analytical methods to determine the ratio.
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