Iridium‐Catalyzed Enantioselective Allylic Substitution of Unstabilized Enolates Derived from α, β‐Unsaturated Ketones
M Chen, JF Hartwig - Angewandte Chemie, 2014 - Wiley Online Library
Angewandte Chemie, 2014•Wiley Online Library
We report Ir‐catalyzed, enantioselective allylic substitution reactions of unstabilized silyl
enolates derived from α, β‐unsaturated ketones. Asymmetric allylic substitution of a variety
of allylic carbonates with silyl enolates gave allylated products in 62–94% yield with 90–
98% ee and> 20: 1 branched‐to‐linear selectivity. The synthetic utility of this method was
illustrated by the short synthesis of an anticancer agent, TEI‐9826.
enolates derived from α, β‐unsaturated ketones. Asymmetric allylic substitution of a variety
of allylic carbonates with silyl enolates gave allylated products in 62–94% yield with 90–
98% ee and> 20: 1 branched‐to‐linear selectivity. The synthetic utility of this method was
illustrated by the short synthesis of an anticancer agent, TEI‐9826.
Abstract
We report Ir‐catalyzed, enantioselective allylic substitution reactions of unstabilized silyl enolates derived from α,β‐unsaturated ketones. Asymmetric allylic substitution of a variety of allylic carbonates with silyl enolates gave allylated products in 62–94 % yield with 90–98 % ee and >20:1 branched‐to‐linear selectivity. The synthetic utility of this method was illustrated by the short synthesis of an anticancer agent, TEI‐9826.
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