Trimethyl Orthoacetate and Ethylene Glycol Mono‐Vinyl Ether as Enolate Surrogates in Enantioselective Iridium‐Catalyzed Allylation |
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| Authors: | Yeshua Sempere Prof Dr Erick M Carreira |
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| Institution: | Laboratorium für Organische Chemie, HCI H335, Eidgen?ssische Technische Hochschule Zürich, Zürich, Switzerland |
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| Abstract: | Trimethyl orthoacetate and ethylene glycol mono‐vinyl ether are employed in iridium‐catalyzed enantioselective allylation reactions. The method documented enables their convenient use as surrogates for silyl ketene acetals and silyl enol ethers to prepare γ,δ‐unsaturated esters and protected aldehydes with excellent enantioselectivity. The utility of this novel method has been demonstrated by its implementation in a formal enantioselective synthesis of the meroterpenoid (+)‐conicol. |
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| Keywords: | allylation asymmetric catalysis iridium total synthesis trimethyl orthoacetate |
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