Organic Reaction Mechanisms 1997
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! " & #
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OH |
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OH |
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But |
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Condition (i) |
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85 |
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15 |
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(91%) |
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Condition (ii) |
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45 |
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(50%) |
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Condition (i) |
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57 |
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(91%) |
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Condition (ii) |
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54 |
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(86%) |
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Reagents: (i) catalytic OsO4, NMO, acetone, H2O
(ii) OsO4 (1 mol%), Me3NO 2H2O (1.3 equiv.), CH2Cl2
SCHEME 1
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# M |
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M M
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OMe |
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MeO |
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O N |
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(5)
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#
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J
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K K
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# $
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J
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J J
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M J
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M M M M
M M M #M
M M
! " ! " $
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J
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ButOO I O
O
(6)
# J M
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C8H17 |
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Y |
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O O |
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O |
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AcO |
AcO |
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OH |
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OR |
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OR |
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(7) |
(8) |
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a; R = Pri, Y = C H |
17 |
b; R = Me, Y = H |
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8 |
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K K
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K K
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M
O |
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* |
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* |
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O |
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diol/H+ |
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peracid |
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H3O+ |
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+ |
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–diol |
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R |
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R |
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R |
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R |
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(9) |
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M
M
K
M K
J
J
J
J J
J