The intermediate is a hemiacetal that hydrolyses to a

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Unformatted text preview: p. 399 in the textbook The first reaction is an E1cB elimination of a β- hydroxy- ketone. The product is still chiral although it has lost one stereogenic centre. The other (quaternary) centre is not affected by the reaction so the product is enantiomerically pure. O O O O H O –H HO HO H OH H OH OH H O The second example already has an electron- rich alkene (an enol ether) present in the starting material so this is more of an E1 than an E1cB mechanism. The intermediate is a hemiacetal that hydrolyses to a ketone (p. 224 in the textbo...
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This document was uploaded on 02/10/2014.

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