13694-33-2Relevant 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 (2007/10/03)
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
Chromium(ii)-mediated reactions of iodonium tetrafluoroborates with aldehydes: Umpolung of reactivity of diaryl-, alkenyl(aryl)-, and alkynyl(aryl)iodonium tetrafluoroborates
Chen, Da-Wei,Ochiai, Masahito
, p. 6804 - 6814 (2007/10/03)
The method described herein allows us, for the first time, to perform umpolung of reactivity of diaryl-, alkenyl(aryl)-, and alkynyl(aryl)iodonium tetrafluoroborates. The method involves generation of organochromium(III) species via reaction of iodonium salts with anhydrous chromium dichloride, followed by their nucleophilic addition to aldehydes to yield alcohols. In contrast to the reaction of aryl and alkenyl halides with chromium dichloride, these iodonium salts are so active that organochromium(III) could be generated without using a nickel catalyst. Substituent effects of unsymmetrically substituted diaryliodonium salts on the product profiles are in good agreement with the reported mode of decomposition of the intermediate unsymmetrical diaryliodanyl radicals. Alkenyl(mesityl)iodonium tetrafluoroborates undergo exclusive alkenylation of aldehydes with no signs of the formation of an arylation product.
Efficient routes to cyclic 2,3-epoxyalcohols from cycloalkenyl ketones, via cycloalkenyl alcohols
Marson,Walker,Pickering,Harper,Wrigglesworth,Edge
, p. 10317 - 10338 (2007/10/02)
The minimising of torsional strain and non-bonding interactions is proposed as the explanation of high diastereoselectivity observed in the epoxidation of cycloalkenyl alcohols, reported for twenty three examples. The resulting 2,3-epoxyalcohols are key i
