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For examples in photochemistry of an increased steric demand of polar substituents through hydrogen bonding, see: a) U. Lindemann, G. Reck, D. Wulff-Molder, P. Wessig, Tetrahedron 1998, 54, 2529-2544;
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We have attempted to perform this reaction enantioselectively. The use of acetate as the nucleophile in the presence of a chiral Co-salen complex resulted in the formation of the product in 36% yield with 45% ee: a E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776;
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We have attempted to perform this reaction enantioselectively. The use of acetate as the nucleophile in the presence of a chiral Co-salen complex resulted in the formation of the product in 36% yield with 45% ee: a) E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776;
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53549114662
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The published 13C NMR spectroscopic data[1b] are shifted upfield consistently by 2 ppm as a result of a different calibration. In our experiments, D4]MeOH (δ, 49.1 ppm) was employed as an internal standard. We thank Prof. R. L. Edwards and Prof. D. J. Maitland for sharing this information with us
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4]MeOH (δ = 49.1 ppm) was employed as an internal standard. We thank Prof. R. L. Edwards and Prof. D. J. Maitland for sharing this information with us.
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