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4. For the synthetic study on the α-substituted serine derivatives from epoxy alcohols, see:(a) Hatakeyama, S.; Matsumoto, H.; Fukuyama, H.; Mukugi, Y.; Irie, H. J. Org. Chem. 1997, 62, 2275-2279.
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18
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0010558703
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note
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1H NMR (600 MHz) after deprotection of the silyl ethers and converting into the MTPA esters. Katsuki-Sharpless epoxidation of the corresponding allyl alcohols gave optically active products up to 90% ee.
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19
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0010555081
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note
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11. The optical purity of β-siloxy aldehydes was reported to be completely dependent on that of the starting epoxides. see ref. 9.
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20
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0015520853
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12. Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
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37049074416
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13. Irie, H; Nishimura, M.; Yoshida, M.; Ibuka, T. J. Chem. Soc., Perkin Trans, 1 1989, 1209-1210.
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Irie, H.1
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Ibuka, T.4
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24
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0010595503
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note
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3) (6); δ 7.34-7.37 (5H, m), 5.27 (1H, s), 5.23 (1H, d, J = 12.2 Hz), 5.18 (1H, d, J = 12.2 Hz), 3.95-4.08 (1H, m), 3.87-3.70 (1H, m), 3.20 (1H, br.s), 1.48 (3H, s), 1.42 (9H, s); δ 173.3 (s), 155.4 (s), 135.4 (s), 128.6 (d), 128.3 (d), 128.1 (d), 80.3 (s), 67.4 (t), 67.0 (t), 61.0 (s), 28.3 (q), 20.8 (q).
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25
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0010638321
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note
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16. Optical purity of 1 and 2 was determined as follows; saponification of the methyl ester with potassium trimethylsilanolate and deprotection of the Boc group with TFA yielded free amino acids, which were directly analyzed by HPLC using ligand exchange chiral column. (condition: SUMICHIRAL OA-5000 (4.6 mm × 15 cm, Sumika Chemical Analysis Service Ltd.); mobile phase: 2 mM copper (II) sulfate in [water/isopropanol (85/15)]; flow rate: 1.0 ml/min; detector: UV 254 nm; room temperature).
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26
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2542433188
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17. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
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Carlsen, P.H.J.1
Katsuki, T.2
Martin, V.S.3
Sharpless, K.B.4
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