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24
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85088715502
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note
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3CN) at 40 °C gave a 4:1 equilibrium mixture of 4a and 3a after 10 days.
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25
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85088717842
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note
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3 = 1:3.1:2.6) at 40 °C for 24 h resulted in a racemization to 77% ee accompanied with a formation of 14% of 4a. Reaction of (R)-4a under identical conditions resulted in a complete racemization with a formation of 12% of racemic 3a.
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26
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0030575842
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(a) Ishida, T.; Bounds, S. V. J.; Caldwell, J.; Drake, A.; Takeshita, T. Tetrahedron: Asymmetry 1996, 7, 3113-3118.
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Ishida, T.1
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Takeshita, T.5
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28
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4444276636
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Although optically active syn-1,2-diols with extremely high ee's are readily accessible using the Sharpless AD reaction of trans-disubstitued olefins, anti-diols can be obtained with moderate to good ee's from the AD reaction of cis-olefins (syn-1-phenyl-1,2-propanediol 5b with 97% ee vs anti-1-phenyl-1,2-propanediol 5a with 72% ee). (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
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Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
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