Powerful Ti-Crossed Claisen Condensation between Ketene Silyl Acetals or Thioacetals and Acid Chlorides or Acids

Powerful Ti-Crossed Claisen Condensation between Ketene Silyl Acetals or Thioacetals and Acid Chlorides or Acids

A powerful Ti-crossed Claisen condensation between ketene silyl acetals (KSAs) and acid chlorides was successfully performed to give α-monoalkylated esters and thermodynamically unfavorable (less accessible) α,α-dialkylated β-keto esters in good yield (46 examples; 41−98% yield). A closely related r...

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Veröffentlicht in:Organic letters 2006-11, Vol.8 (23), p.5215-5218
Hauptverfasser: Iida, Akira, Nakazawa, Syogo, Okabayashi, Tomohito, Horii, Atsushi, Misaki, Tomonori, Tanabe, Yoo
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container_end_page 5218
container_issue 23
container_start_page 5215
container_title Organic letters
container_volume 8
creator Iida, Akira
Nakazawa, Syogo
Okabayashi, Tomohito
Horii, Atsushi
Misaki, Tomonori
Tanabe, Yoo
description A powerful Ti-crossed Claisen condensation between ketene silyl acetals (KSAs) and acid chlorides was successfully performed to give α-monoalkylated esters and thermodynamically unfavorable (less accessible) α,α-dialkylated β-keto esters in good yield (46 examples; 41−98% yield). A closely related reaction between ketene silyl thioacetals (KSTAs) and acid chlorides also proceeded smoothly to give α-monoalkylated and α,α-dialkylated β-keto thioesters (21 examples; 61−97% yield). The present protocol was extended to the direct condensation of KSAs with carboxylic acids (14 examples; 71−97% yield).
doi_str_mv 10.1021/ol0619361
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