95205-95-1Relevant academic research and scientific papers
Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach
Armstrong, Roly J.,Akhtar, Wasim M.,Frost, James R.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
, (2019/11/13)
A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.
Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5 + 1) Annulation Strategy
Akhtar, Wasim M.,Armstrong, Roly J.,Frost, James R.,Stevenson, Neil G.,Donohoe, Timothy J.
, p. 11916 - 11920 (2018/09/27)
An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, providing direct access to multisubstituted cyclic products with high levels of stereocontrol. This methodology represents a novel (5 + 1) strategy for the stereoselective construction of the cyclohexane core.
Water-compatible iminium activation: Organocatalytic Michael reactions of carbon-centered nucleophiles with enals
Palomo, Claudio,Landa, Aitor,Mielgo, Antonia,Oiarbide, Mikel,Puente, Angel,Vera, Silvia
, p. 8431 - 8435 (2008/09/19)
(Chemical Equation Presented) A pool of water-compatible catalysts, namely the chiral prolinol-based catalysts 1, has been developed for highly enantioselective C-C bond-forming Michael reactions in water (see scheme). The synthesis of (S)-Rolipram, a type IV phosphodiesterase inhibitor, was also demonstrated.
Stereoselective Michael additions of titanium "ate" complexes of ketone and ester enolates
Bernardi, Anna,Dotti, Pierfranco,Poli, Giovanni,Scolastico, Carlo
, p. 5597 - 5606 (2007/10/02)
The conjugate addition of Ti "ate" complexes of ketone and ester enolates to α,β-unsaturated carbonyl compounds was studied. The reaction was found to be highly regio- and stereoselective. Compared to the lithium enolates, ketone enolate Ti complexes show
A HIGHLY STEREOSELECTIVE MICHAEL REACTION OF SIMPLE ESTER ENOLATES TO α,β-UNSATURATED ESTERS
Yamaguchi, Masahiko,Tsukamoto, Michinori,Tanaka, Shinya,Hirao, Ichiro
, p. 5661 - 5664 (2007/10/02)
Under a proper reaction condition, simple ester enolates add to α,β-unsaturated esters highly stereoselectively to give erythro or threo-glutarates.
