110995-44-3Relevant academic research and scientific papers
Direct Stereoselective β-Arylation of Enol Ethers by a Decarboxylative Heck-Type Reaction
Hachem, Mahmoud,Hoarau, Christophe,Schneider, Cédric
, (2020/04/15)
Despite remarkable advances to promote regio- and stereoselective decarboxylative arylation of inactivated olefins with benzoic acid derivatives, methodologies involving hetero-substituted alkenes are still lacking. Herein, PdII-catalyzed decarboxylative Heck coupling of α-alkoxyacrylates with (hetero)aryl carboxylic acids for the stereocontrolled production of (Z)-β-heteroarylated vinyl ethers is reported. This methodology offers a rational and step-economical route to the synthesis of attractive β-arylated α-alkoxy α,β-unsaturated carboxylates family which emerged as a relevant class of building blocks with different applications. Mechanistically, whereas electron rich benzoic acids undergo a PdII-catalyzed decarboxylation, electron-deficient substrates proceed through silver(I)-mediated decarboxylation, explaining thus the formation of stereoisomers (E) and (Z) of β-arylated vinyl ethers in presence of these latter.
THE SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-LEPTOSPHAERIN
Pallenberg, Alexander J.,White, James D.
, p. 5591 - 5594 (2007/10/02)
A synthesis of (+)-leptosphaerin (1), a metabolite of the marine ascomycete Leptosphaeria oraemaris (Linder), was accomplished from (R)-glyceraldehyde by a route that confirms the structural assignment and establishes the absolute configuration of 1 as (4S,5R).
