Abstract
A Ru(ii)-catalyzed direct access to various functionalized allenoic acids via C-H allenylation of readily available aryl carboxylic acids with propargylic acetates is reported. Axially chiral allenoic acids could be obtained in high ee by using optically active propargylic acetates through a chirality transfer strategy.
Highlights
All publication charges for this article have been paid for by the Royal Society of Chemistry
Chiral allenoic acids could be obtained in high ee by using optically active propargylic acetates through a chirality transfer strategy
The synthesis of functionalized allenes is of crucial importance
Summary
All publication charges for this article have been paid for by the Royal Society of Chemistry. A Ru(II)-catalyzed direct access to various functionalized allenoic acids via C–H allenylation of readily available aryl carboxylic acids with propargylic acetates is reported. Chiral allenoic acids could be obtained in high ee by using optically active propargylic acetates through a chirality transfer strategy. We wish to report the realization of Ru-catalyzed synthesis of allenoic acids via direct C–H allenylation of benzoic acids (Scheme 1f). The reaction could proceed in dioxane, DCE, CH3CN, THF, and even in water, albeit affording the monoallenylation product 3aa and the double allenylation product 4aa in rather low yields (Table 1, entries 2–6). The yield could be greatly improved when the reaction was conducted in MeOH: 36% yield of the monoallenylation product 3aa and 16% yield of the double allenylation product 4aa were obtained (Table 1, entry 7).
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