458557-46-5Relevant academic research and scientific papers
Tandem Asymmetric Conjugate Addition-Silylation of Enantiomerically Enriched Zinc Enolates. Synthetic Importance and Mechanistic Implications
Knopff, Oliver,Alexakis, Alexandre
, p. 3835 - 3837 (2002)
(Matrix Presented) The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or w
One-pot enantioselective formation of eight-membered rings from alkenyl fischer carbene complexes and ketone enolates
Barluenga, Jose,Dieguez, Alejandro,Rodriguez, Felix,Florez, Josefa,Fananas, Francisco J.
, p. 9056 - 9057 (2002)
Eight-membered carbocycles with up to five new stereogenic centers are enantioselectively obtained following a one-pot procedure that involves the coupling of three components: an alkenyl Fischer carbene complex, a ketone enolate, and allyl lithium. Copyr
Tandem enantioselective conjugate addition--cyclopropanation. Application to natural products synthesis.
Alexakis, Alexandre,March, Sebastien
, p. 8753 - 8757 (2007/10/03)
A tandem asymmetric conjugate addition-cyclopropanation was developed, in which a cyclic or linear enone was converted to a TMS-protected 3-substituted-cyclopropanol in an efficient one-pot reaction. These compounds were then selectively cleaved to yield alpha-methyl-beta-alkyl ketones, alpha-methylene-enones, or chain extended gamma-alkyl-enones. This methodology was applied to the formal total synthesis of (-)-(S,S)-clavukerin A and (+)-(R,S)-isoclavukerin.
