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From Protected -Hydroxy Acylsil­anes to Functionalized Silyl Enol Ethers and Applications in Mukaiyama Aldol Reactions

Abstract : By starting from protected -hydroxy acylsilanes, two complementary strategies were designed to prepare stereoselectively either E or Z silyl enol ethers. These routes exhibit good tolerance for different substituents on the starting aldol-type product, as well as the choice of the hydroxyl-protecting group and the acylsilane moiety. Further, by varying the nature of the sulfone used in these reactions it proved possible to introduce different substituents on the enol ether system. Representative examples of Mukaiyama aldol reactions were performed to demonstrate the usefulness of this approach towards polypropionate fragments
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01254804
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Submitted on : Tuesday, January 12, 2016 - 4:46:46 PM
Last modification on : Thursday, March 5, 2020 - 2:04:37 PM

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Johal Ruiz, Nagaraju Karre, Thierry Roisnel, Srivari Chandrasekhar, René Grée. From Protected -Hydroxy Acylsil­anes to Functionalized Silyl Enol Ethers and Applications in Mukaiyama Aldol Reactions. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2016, 2016 (4), pp.773-779. ⟨10.1002/ejoc.201501344⟩. ⟨hal-01254804⟩

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