145451-77-0Relevant academic research and scientific papers
Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone
Ito, Masato,Kitahara, Sachiko,Ikariya, Takao
, p. 6172 - 6173 (2005)
Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-κ2-P,N]-KOt-Bu (Cp* = η5-C5(CH3)5) under mild conditions. Mechanistic consideration based on isotope-labeling experiments indicated the present reaction is applicable to the asymmetric isomerization of racemic sec-allylic alcohols with a prochiral olefin via dynamic kinetic resolution. A concise asymmetric synthesis of muscone has been achieved, where the asymmetric isomerization using an optically active ligand is a key reaction. Copyright
Episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates
Dishington, Allan P.,Douthwaite, Richard E.,Mortlock, Andrew,Muccioli, Adriano B.,Simpkins, Nigel S.
, p. 323 - 337 (2007/10/03)
Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and Bu′-P4 phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2. The structure of a trisilylated episulfone product, 2a, was determined by X-ray crystallography. In the absence of Me3SiCl, reaction of episulfones with lithium diisopropylamide results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.
