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1-Bromo- and 1-chloro-2-propanol are commercially available as a mixture of secondary and primary alcohols in a 70:30 ratio. However, purification of the secondary alcohol was possible by simple partial esterification reaction with benzoyl chlorideat0°C.
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1-Bromo- and 1-chloro-2-propanol are commercially available as a mixture of secondary and primary alcohols in a 70:30 ratio. However, purification of the secondary alcohol was possible by simple partial esterification reaction with benzoyl chlorideat0°C.
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59
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60849103649
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Diastereoisomers anti and syn of the α,α'- disubstituted linear ethers are defined as described in the figure below:
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Diastereoisomers anti and syn of the α,α'- disubstituted linear ethers are defined as described in the figure below:
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-
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60
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1242348732
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For previously reported syntheses of lauthisan, see: a
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60849109073
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[6a];
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60849102624
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[17];
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40749114805
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The synthesis of 18a with higher enantiomeric purity could be achieved by kinetic resolution of racemic allylic alcohol (±)- 18a by using (-)-DET, see: V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 6237-6240.
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80
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34548682494
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The enantiomeric excess was determined by Mosher's ester. See the Supporting Information
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60849104652
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[17]
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[17]
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84
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60849092697
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See the Supporting Information
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See the Supporting Information
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85
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0034704297
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6-cycloalkyne ethers, see: a) T.-Z. Liu, J.-M. Li, M. Isobe, Tetrahedron 2000, 56, 10209-10219;
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86
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60849090904
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[11]
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[11]
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Martín, V.S.4
-
88
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60849087221
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2 as catalyst.
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2 as catalyst.
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