Iridium‐Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α‐Alkoxy Ketones |
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| Authors: | Xingyu Jiang Wenyong Chen Prof John F Hartwig |
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| Institution: | 1. Department of Chemistry, University of California, CA, 94720, USA;2. Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, CA, USA |
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| Abstract: | The asymmetric alkylation of acyclic ketones is a longstanding challenge in organic synthesis. Reported herein are diastereoselective and enantioselective allylic substitutions with acyclic α‐alkoxy ketones catalyzed by a metallacyclic iridium complex to form products with contiguous stereogenic centers derived from the nucleophile and electrophile. These reactions occur between allyl methyl carbonates and unstabilized copper(I) enolates generated in situ from acyclic α‐alkoxy ketones. The resulting products can be readily converted into enantioenriched tertiary alcohols and tetrahydrofuran derivatives without erosion of enantiomeric purity. |
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| Keywords: | alkylation asymmetric catalysis diastereoselectivity iridium ketones |
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