ORGN 600 |
Stereoselective synthesis of primary and secondary allylic alcohols via rhenium-catalyzed isomerization reactions
| Christie Morrill and Robert H. Grubbs. Division of Chemistry and Chemical Engineering, California Institute of Technology, Mail Code 164-30, Pasadena, CA 91125 |
| The complex ReO3OSiPh3 is an efficient catalyst for the isomerization of allylic alcohols. This isomerization reaction is typically an equilibrium process and thus results in a mixture of isomers. However, when substrates are chosen such that the desired product is a conjugated system and the starting material is not conjugated (R1 = aryl), quantitative conversion to product is observed. Additionally, when the products are primary alcohols (R2 = H), addition of a silylating agent to the reaction results in nearly quantitative conversion to the desired product, due to selective protection of the primary alcohol. Thus in this latter case, both conjugated and non-conjugated compounds can be synthesized in high yield. All of these isomerization reactions proceed with high E-selectivity, regardless of the stereochemistry of the starting material. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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