92372-49-1Relevant academic research and scientific papers
Construction of Medium- and Large-Sized Cyclic β-Keto Esters (or Nitriles) via One-Pot Three-Carbon Ring Expansion of Carbocyclic β-Keto Esters and Its Application to the Synthesis of (-)-Muscone
Xie, Zhuo-Feng,Sakai, Kiyoshi
, p. 820 - 826 (1990)
A one pot, three-carbon ring expansion involving intramolecular aldol condensation and subsequent retro-aldol cleavage is induced by treatment of β-keto esters with potassium tert-butoxide in dimethyl sulfoxide to afford functionalized 8-,9-,10-, and 15-membered rings, respectively.The stereochemistry of intermediate 21 was established to be a cis-fused carbocyclic ring system with the methyl ketone in the cis position.The mechanism for the three-carbon ring expansion is explained by considering the dual function of the electron-withdrawing group (EWG).An iterativering expansion was accomplished by the facile conversion of 8 to 20.Application of this ring expansion method to the synthesis of (-)-muscone further attests to the generality of this reaction.
Synthetic Approach to Medium-sized Cycloalkanones. A One-pot Three-carbon Ring Expansion of Carbocyclic β-Keto Esters
Xie, Zhuo-Feng,Suemune, Hiroshi,Sakai, Kiyoshi
, p. 612 - 613 (2007/10/02)
By treatment with ButOK in Me2SO, carbocyclic β-keto-esters (5, 6, and 7-membered rings) with a 4-oxopentyl function at the α-position afforded three-carbon ring expansion products (8, 9, and 10-membered rings, respectively).
