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Isolation of the alcohol 4 resulting from pathway c circumvents the potential problem of loss of optical purity due to poor regioselectivity. Advantage has been taken of this fact in more than one synthesis involving optically active epichlorohydrin
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Isolation of the alcohol 4 resulting from pathway c circumvents the potential problem of loss of optical purity due to poor regioselectivity. Advantage has been taken of this fact in more than one synthesis involving optically active epichlorohydrin. (a) Yo, E.; Nakagawa, K.; Hoshino, Y. Chem. Pharm. Bull. 1981, 29, 2157.
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The pronounced steric hindrance of 2,4,6-triisopropylbenzene-sulfonyl chloride has been exploited in a variety of applications, particularly in carbohydrate and nucleoside chemistry. See: Eds.; Pergamon: Oxford, Vol. 5 and references cited therein.
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The pronounced steric hindrance of 2,4,6-triisopropylbenzene-sulfonyl chloride has been exploited in a variety of applications, particularly in carbohydrate and nucleoside chemistry. See: Comprehensive Organic Chemistry; Barton, D., Ollis, W.,D., Eds.; Pergamon: Oxford, 1979; Vol. 5 and references cited therein.
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The preparation of oxazolines from epoxides by treatment with a nitrile and BF3.OEt2has been reported previously
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Melting points are uncorrected. Flash chromatography was performed on Merck silica gel 60 (230–400 mesh) as described by Still All commercial reagents were used as received unless otherwise noted. (±)-Glycidol (Aldrich) was distilled under reduced pressure and stored at -20 °C. (2R)-and (2S)-glycidol were prepared as previously described.2 Copper(I) iodide (99.999%) was used as received from Cerac.
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Melting points are uncorrected. Flash chromatography was performed on Merck silica gel 60 (230–400 mesh) as described by Still [Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923]. All commercial reagents were used as received unless otherwise noted. (±)-Glycidol (Aldrich) was distilled under reduced pressure and stored at -20 °C. (2R)-and (2S)-glycidol were prepared as previously described.2 Copper(I) iodide (99.999%) was used as received from Cerac.
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