lecture 13

lecture 13 - 2000 , , 9328-9329. Hioki, H.; Kanehara, C.;...

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O OH OH OH OH HO O O O O O Me Me HO Me Me OH H Me H Me H H Me H Me H R R'' OH R' R R'' OH R' O R R'' OH R' O HO OH R R O H R R'' OH R' HO SPh R SPh OAc R SPh R R''' OH R' R'' R R''' OH R' R'' O R R'' H R' R R'' R' OH OH R R' R R' O H H R R'' R' R R'' O R' Chem 215 Lecture 13: Stereochemical Strategies Targeted toward Oxygenated Stereocenters Monday, November 5, 2007 Reading Assignment: Handouts: Jacobsen Asymmetric Epoxidation Reaction, Shi Epoxidation, Jacobsen Catalytic Asymmetric Epoxide-Opening Reaction, Transformations of 2,3-Epoxy Alcohols, Asymmetric Diels-Alder Reactions, and The Noyori Asymmetric Hydrogenation Reaction Syntheses Discussed: References: L-Hexoses: Koo, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A., III; Sharpless, K. B.; Walker, F. J.; Tetrahedron 1990 , 46 , 245-264. Glabrescol: Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 2000 , 122 , 4831-4832. Xiong, Z.; Corey, E. J.
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Unformatted text preview: 2000 , , 9328-9329. Hioki, H.; Kanehara, C.; Ohnishi, Y.; Umemori, Y.; Sakai, H.; Yoshio, S.; Matsushita, M.; Kodama, M. Angew. Chem., Int. Ed. Engl. 2000 , 39 , 2552-2554. Partial List of Transforms Covered: Sharpless Asymmetric Epoxidation Payne Rearrangement/Nucleophilic Opening of Terminal Epoxides Pummerer Rearrangement Epoxides from 1,2-Diols 1,2-Diols from Epoxides Sharpless Kinetic Resolution Sharpless Asymmetric Dihydroxylation Jacobsen Asymmetric Epoxidation Shi Asymmetric Epoxidation Jacobsen Hydrolytic Kinetic Resolution Graphical Transform Guide: Shair L-Hexoses Glabrescol RCHO R SPh OAc HO OH R R O H R O R O R O R Nu OH...
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