191531-86-9Relevant academic research and scientific papers
Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives
Allin, Steven M.,Northfield, Christopher J.,Page, Michael I.,Slawin, Alexandra M.Z.
, p. 1715 - 1721 (2000)
New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic γ-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophiles. Removal of the phenylglycinol
A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives
Allin, Steven M.,Northfield, Christopher J.,Page, Michael I.,Slawin, Alexandra M. Z.
, p. 3627 - 3630 (1997)
Condensation of 2-formylbenzoic acid with α-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic γ-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal a
A novel and highly stereoselective route for the synthesis of non-racemic 3-substituted isoindolin-1-one targets
Hemming, Ryan A.,Bell, Megan,Duffy, Liam J.,Bristow, Jonathan,Wallis, John D.,Allin, Steven M.,Bulman Page, Philip C.
, p. 121 - 127 (2018/11/30)
A new, versatile and highly stereoselective approach for the synthesis of non-racemic 3-substituted isoindolin-1-ones is described from a readily available chiral template. The potential of this new protocol is demonstrated through the synthesis of an enantiomerically enriched 3-alkyl N-H isoindolin-1-one target with an e.e. of 98%.
Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction
Maity, Arnab Kumar,Roy, Sujit
, p. 2627 - 2642 (2014/09/30)
The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.
Meyers' bicyclic lactam formation under mild and highly stereoselective conditions
Penhoat, Ma?l,Leleu, Stephane,Dupas, Georges,Papamica?l, Cyril,Marsais, Francis,Levacher, Vincent
, p. 8385 - 8389 (2007/10/03)
New and mild conditions to prepare chiral bicyclic lactams in high yields and high diastereoselectivities are reported herein. This approach based on the activation of the carboxylic acid by means of Mukaiyama's reagent is an excellent alternative to Meye
