90392-95-3Relevant articles and documents
Enantioselective Redox-Neutral Coupling of Aldehydes and Alkenes by an Iron-Catalyzed "catch-Release" Tethering Approach
Li, Jing,Preinfalk, Alexander,Maulide, Nuno
, p. 143 - 147 (2019)
The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form "branched" products. Herein, we present a directed enantio- and diastereoselective alkylation of aldehydes with simple olefins to selectively yield linear coupling products. This is achieved by redox-neutral remote functionalization, whereby a tethering "catch-release" strategy decisively solves the key problems of reactivity and selectivity.
Cyclopentadienyl Ruthenium(II) Complex-Mediated Oxidation of Benzylic and Allylic Alcohols to Corresponding Aldehydes
Chern, Ching-Yuh,Tseng, Ching-Chun,Hsiao, Rong-Hong,Wong, Fung Fuh,Kuo, Yueh-Hsiung
, (2019/09/13)
This work reports an efficient method for the oxidation reaction of aliphatic, aromatic allylic, and benzylic alcohols into aldehydes catalyzed by the cyclopentadienyl ruthenium(II) complex (RuCpCl(PPh3)2) with bubbled O2. Through further optimizing controlled studies, the tendency order of oxidation reactivity was determined as follows: benzylic alcohols > aromatic allylic alcohols >> aliphatic alcohols. In addition, this method has several advantages, including a small amount of catalyst (0.5 mol%) and selective application of high discrimination activity of aliphatic, aromatic allylic, and benzylic alcohols.
Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers
Kawajiri, Takahiro,Ohta, Reiya,Fujioka, Hiromichi,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 374 - 377 (2018/02/27)
The aldol reaction using aldehyde-derived silyl enolates as nucleophiles with aromatic aldehydes chemoselectively proceeded in the presence of silyl triflate and 2,2′-bipyridyl to produce β-siloxy aldehydes, while the aliphatic aldehydes were completely recovered. The unprecedented chemoselectivities depend on the reactivities of the pyridinium-type intermediates derived from the aromatic and aliphatic aldehydes.