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79952363060
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note
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Determination of the relative stereochemistry of compound 4 by NOE effects was not conclusive.
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27
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79952361887
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note
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cf. Ref. 4e, the assignment of an anti stereochemistry of β-hydroxy-α-amino esters were also obtained through coupling constants comparison of corresponding cyclic carbamate after the removal of Boc group followed by treatment of the corresponding product with triphosgene. However, absolute stereochemistry assignment was not determined.
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28
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0141712450
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K.B. Sharpless, W. Amberg, L.B. Youssef, G.A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, and X.-L. Zhang J. Org. Chem. 57 1992 2768
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30
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79952363905
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note
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Even though a small amount of epimerization may happen at the α-position of ester, it is unlikely to epimerize the stereogenic center at the benzylic position. Therefore, we can correlate four isomers with ester 3 for a comparison to assign the absolute stereochemistry.
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32
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77955169875
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G. Yang, H. Tran, W. Shi, T.L. Lowary, and Y. Xu Chirality 22 2010 734 and the references cited therein
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33
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79952364575
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note
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cf. Refs. 4b and 4c, syn β-hydroxyl α-amino esters were reported when Cbz protected substrate 1h was used under similar conditions.
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