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24
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85033167990
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note
-
Only one enantiomer is shown in the scheme for convenience.
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25
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37049106918
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26
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85033166434
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note
-
Conditions for preparative chromatography of 1: column, CHIRALCEL OD (2 cm φ × 25 cm); eluent, ethanol; flow rate, 3.5 mL/min; detection, UV 254 nm; retention times, 55.1 and 83.0 min: conditions for analytical chromatography of 1: column, CHIRALCEL OD (0.46 cm φ × 5 cm); eluent, ethanol; flow rate, 0.2 mL/min; detection, UV 254 nm; retention times, 11.3 and 16.7 min.
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27
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85033165208
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note
-
Conditions for preparative chromatography of 2: column, CHIRALCEL OD (2 cm φ × 25 cm); eluent, ethanol; flow rate, 4.0 mL/min; detection, UV 254 nm; retention times, 78.5 and 156 min: conditions for analytical chromatography of 2: column, CHIRALCEL OD (0.46 cm φ × 5 cm); eluent, ethanol; flow rate, 0.5 mL/min; detection, UV 254 nm; retention times, 7.6 and 14.1 min.
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28
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85033181521
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note
-
1H NMR.
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29
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85033179087
-
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note
-
Conditions for preparative chromatography of 19: column, CHIRALCEL OD (2 cm φ × 25 cm); eluent, ethanol; flow rate, 1.5 mL/min; detection, UV 254 nm; retention times, 89.5 and 95.6 min: conditions for analytical chromatography of 19: column, CHIRALCEL OD (0.46 cm φ × 5 cm + 0.46 cm φ × 25 cm); eluent, ethanol; flow rate, 0.5 mL/min; detection, UV 254 nm; retention times, 23.7 and 29.1 min. The second fraction was obtained in >99% ee by repetition of the optical resolution.
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31
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0001688336
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Shinkai, S.; Kawanabe, S.; Kawase, A.; Yamaguchi, T.; Manabe, O. Bull. Chem. Soc. Jpn. 1988, 61, 2095-2102.
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Shinkai, S.1
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Manabe, O.5
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32
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85033176486
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note
-
Although trifluoroacetic acid was also used as an acid catalyst, syn/anti ratio was unable to be determined, because BNAH was decomposed by the acid very quickly.
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-
-
-
34
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0003191423
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-1: Ohno, A.; Yamamoto, H.; Okamoto, T.; Oka, S.; Ohnishi, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2385-2386.
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35
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0008116136
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For the contribution of a ternary complex in the reaction, see: Ohno, A.; Yasui, S.; Nakamura, K.; Oka, S. Bull. Chem. Soc. Jpn. 1978, 51, 290-293.
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36
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33845561800
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It has been confirmed that the conformation at the side-chain carbamoyl group does not affect stereochemistry of the reaction largely: Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036-7040.
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0024286097
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Pai, E. F.; Karplus, P. A.; Schultz, G. E. Biochemistry 1988, 27, 4465-4474.
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