5_6_05 - 2004 , 37 , 488. O O O O O O O 2 O O O O O K t N N...

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Massachusetts Institute of Technology Organic Chemistry 5.512 May 6, 2005 Prof. Rick L. Danheiser Unit 10 Stereocontrolled Epoxidation l i i l l i i i i ( ) i l i l i l i Substrate Contro : 1,2-Asymmetr c Induct on Reagent Contro : Sharp ess-Katsuk Asymmetr c Epox dat on AE Synthet c E aborat on of AE Products Reagent Contro : Jacobsen-Katsuk AE Reagent Contro : Sh AE Reviews "Asymmetric Epoxidation of Unfunctionalized Olefins and Related Reactions" Katsuki, T. In Catalytic Asymmetric Synthesis ; Ojima, I., Ed.; Wiley-VCH, 2000, pp 287-326. "Asymmetric Catalysis of Epoxide Ring-Opening Reactions" Jacobsen, E. N. Acc. Chem. Res. 2000 , 33 , 421. "Organocatalytic Asymmetric Epoxidation of Olefins by Chiral Ketones" Shi, Y.
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Unformatted text preview: 2004 , 37 , 488. O O O O O O O 2 O O O O O K t N N t O O H H NCO Et s f r Shi Ep id ti-Bu -Bu -Bu Mn -Bu Cl Jacobsen Manganese Salen Catalyst e one o ox a on E. N. Jacobsen et al. Organic Syntheses CollVol. 10 , 29 0.6 mol% (salen)MnCl 1.3 equiv 10% aq NaOCl CH 2 Cl 2-N + 3 mol% Ph O O 71% 84-86% ee Y. Shi et al. Organic Syntheses 80 , 9 CH 3 Ph Ph 1.5 equiv oxone 35 mol% ketone MeOCH 2 OMe-CH 3 CN aq buffer solutions 0 C, 3.5 h 90-94% 89% ee 4 equiv 30% H 2 O 2 10 mol% ketone aq CH 3 CN aq buffer solutions 0 C, 6 h 79-92% 94-95% ee O CH 3 Ph Ph O...
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5_6_05 - 2004 , 37 , 488. O O O O O O O 2 O O O O O K t N N...

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