3epoxidation - Epoxidation pp. 167-168 Freccero, M.;...

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Epoxidation pp. 167-168 Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. Org. Chem. 2000, 65, 2030. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997 , 119 , 3385. p. 171 1,3-diaxial interaction trans -decalin half-chair
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ansition metal- atalyzed enbest epoxidation Epoxidation of Allyl Alcohol transition metal catalyzed epoxidation p. 180 Henbest epoxidation p. 181 relative rate PhCO 3 H relative rate VO(acac) 2 t -BuOOH O OH OH 1.00 O OH OH 1.00 O 0.55 O >200 O O Me Me t -Bu O 0.067 V O O O RO Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993 , 93 , 1307.Henbest, H. B.; Wilson, R. A. I. J. Chem. Soc. 1957 , 1958. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973 , 95 , 6136. O
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OH OH OH O O (+)-DIPT Ti(Oi-Pr) 4 H H H + CH 2 Cl 2 –20 ºC erythro threo 98 : 2 ( S ) OH OH OH O O + (+)-DIPT Ti(Oi-Pr) 4 H H H CH 2 Cl 2 –20 ºC erythro threo 38 : 62 ( R ) lative rate 104 Sharpless, K. B., et al. J. Am. Chem. Soc. 1981 , 103 , 6237. relative rate
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3epoxidation - Epoxidation pp. 167-168 Freccero, M.;...

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