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  • Ti-crossed-Claisen condensation between carboxylic esters and acid chlorides or acids: a highly selective and general method for the preparation of various beta-keto esters.

Ti-crossed-Claisen condensation between carboxylic esters and acid chlorides or acids: a highly selective and general method for the preparation of various beta-keto esters.

Journal of the American Chemical Society (2005-03-03)
Tomonori Misaki, Ryohei Nagase, Kunshi Matsumoto, Yoo Tanabe
RESUMEN

Ti-crossed-Claisen condensation between a 1:1 mixture of carboxylic esters and acid chlorides promoted by TiCl4-Bu3N-N-methylimidazole proceeded successfully to give various beta-keto esters in good yields with excellent selectivities (19 examples, approximately 48-95% yield; cross/self-selectivity = approximately 96/4-99/1). The present method was extended to the condensation between a 1:1 mixture of carboxylic acids and carboxylic esters (six examples, approximately 70-92% yield; cross/self-selectivity = approximately 91/9-99/1). To demonstrate the utility of the present two Ti-crossed-Claisen condensations, we performed a couple of efficient short-step syntheses of two natural, representative, and useful perfumes, cis-jasmone and (R)-muscone.

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Sigma-Aldrich
cis-Jasmone, stabilized
Supelco
Jasmone, analytical standard