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The coordination of a tricarbonylchromium fragment to the arene ring was found to also increase the diastereoselectivity in the asymmetric allylboration of aromatic aldehydes: Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143.
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Authentic stereodefined anti-N-tosyl-2-amino-1,2-diphenylethyl alcohol derivative was prepared by the following literature procedure: (a) Davis, F. A.; Hague, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021.
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85034525324
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Similarly, the cross-coupling of N-tosyl ferrocenylideneamine (1) with benzaldehydes or the corresponding chromium complexes gave exclusively anti-β-amino alcohols under the same conditions: unpublished results
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Similarly, the cross-coupling of N-tosyl ferrocenylideneamine (1) with benzaldehydes or the corresponding chromium complexes gave exclusively anti-β-amino alcohols under the same conditions: unpublished results.
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43
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85034526552
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A homo-coupling 1,2-diol was in 80% yield as a major product
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A homo-coupling 1,2-diol was in 80% yield as a major product.
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44
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0026101096
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Enantiomerically pure chromium complexes were obtained by optical resolution of diastereomers derived from L-valinol: Bromley, L. A.; Davies, S. G.; Goodfellow, C. L. Tetrahedron: Asymmetry 1991, 2, 139.
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Bromley, L.A.1
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Goodfellow, C.L.3
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45
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85034528322
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Optical purities of 11 and chromium-free 12 were determined by chiral HPLC. For racemic 11: chiralcel OD-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min, 40°C, retention time 33.1 and 36.0 min. For racemic 12: chiralcel OJ-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min. 40°C, retention time 20.4 and 25.0 min
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Optical purities of 11 and chromium-free 12 were determined by chiral HPLC. For racemic 11: chiralcel OD-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min, 40°C, retention time 33.1 and 36.0 min. For racemic 12: chiralcel OJ-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min. 40°C, retention time 20.4 and 25.0 min.
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46
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85034525502
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The absolute configuration of the syn-coupling product 12 was determined as (R,R)-configuration by comparison of the optical rotation sign of authentic syn-β-amino alcohol derived from (R)-2-phenylglycine according to ref 8c
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The absolute configuration of the syn-coupling product 12 was determined as (R,R)-configuration by comparison of the optical rotation sign of authentic syn-β-amino alcohol derived from (R)-2-phenylglycine according to ref 8c.
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47
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0002933593
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Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT
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0000178635
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