Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation. A study in the correlation of the enol ether chain length and enantioselectivity |
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Authors: | Marcune Benjamin F Karady Sandor Reider Paul J Miller Ross A Biba Mirlinda DiMichele Lisa Reamer Robert A |
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Affiliation: | Department of Process Research, Merck and Co., P.O. Box 2000, Rahway, New Jersey 07765, USA. ben_marcune@merck.com |
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Abstract: | The Sharpless asymmetric dihydroxylation reaction of enol ethers derived from their corresponding cyclic ketones, gave alpha-hydroxyketones with high enantioselectivity. The enantiomeric excess was found to be proportional to the length of the unbranched enol ether chain with a maximum ee for the pentyl enol ether. An efficient synthesis of alpha-hydroxy chromanone in >90% ee was demonstrated using this method. |
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