292163-77-0Relevant academic research and scientific papers
Palladium-catalyzed O-allylation of α-hydroxy carbonyl compounds
Schmidt, Bernd,Nave, Stefan
, p. 531 - 537 (2007/10/03)
α-Hydroxy carbonyl compounds undergo smooth O-allylation using allylic carbonates and Pd(0) catalysts. This method has significant advantages over other O-allylation methods as it provides a solution to several problems previously observed for this synthe
Ruthenium-catalyzed olefin metathesis double-bond isomerization sequence
Schmidt, Bernd
, p. 7672 - 7687 (2007/10/03)
A novel ruthenium-catalyzed tandem ring-closing metathesis (RCM) double-bond isomerization reaction is described in this paper. The utility of this method for the efficient syntheses of five-, six-, and seven-membered cyclic enol ethers is demonstrated. It relies on the conversion of a metathesis-active ruthenium carbene species to an isomerization-active ruthenium-hydride species in situ. This conversion is achieved by using various additives. Scope and limitations of the different protocols are discussed, and some mechanistic considerations based on 31P and 1H NMR spectroscopic studies are presented.
Diastereoselective Ring-Closing Metathesis in the Synthesis of Dihydropyrans
Schmidt, Bernd,Wildemann, Holger
, p. 5817 - 5822 (2007/10/03)
An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from α-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.
Synthesis of functionalized 2,3- and 3,4-dihydropyrans starting from α- hydroxycarboxylic esters via RCM
Schmidt, Bernd,Wildemann, Holger
, p. 1591 - 1593 (2007/10/03)
α-Hydroxy carboxylic acids and their derivatives are naturally occurring starting materials for the synthesis of functionalized tetrahydropyrans using ring closing metathesis and base induced epoxide rearrangement as key steps. (S)-Lactic acid methyl este
