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

Akira Iida, Syogo Nakazawa, Tomohito Okabayashi, Atsushi Horii, Tomonori Misaki, and Yoo Tanabe*
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
Org. Lett., 2006, 8 (23), pp 5215–5218
DOI: 10.1021/ol0619361
Publication Date (Web): October 20, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, tanabe@kwansei.ac.jp

Abstract

Abstract Image

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).

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History

  • Published In Issue November 09, 2006
  • Received August 4, 2006

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