6672-30-6Relevant articles and documents
Synthesis of optically pure 3R-methylcyclopentan-1-one from L-(-)-menthol
Ishmuratov,Yakovleva,Ganieva,Gareeva,Muslukhov,Tolstikov
, p. 549 - 551 (2005)
Synthesis of optically pure 3R-methylcyclopentan-1-one using in the key step Dieckmann cyclization of diisopropyl 3R-methylhexan-1,6-dioate, which is accessible from L-(-)-menthol, was proposed. 2005 Springer Science+Business Media, Inc.
Counterion Enhanced Organocatalysis: A Novel Approach for the Asymmetric Transfer Hydrogenation of Enones
Scharinger, Fabian,Márk Pálv?lgyi, ádám,Zeindlhofer, Veronika,Schnürch, Michael,Schr?der, Christian,Bica-Schr?der, Katharina
, p. 3776 - 3782 (2020/06/22)
We present a novel strategy for organocatalytic transfer hydrogenations relying on an ion-paired catalyst of natural l-amino acids as main source of chirality in combination with racemic, atropisomeric phosphoric acids as counteranion. The combination of a chiral cation with a structurally flexible anion resulted in a novel chiral framework for asymmetric transfer hydrogenations with enhanced selectivity through synergistic effects. The optimized catalytic system, in combination with a Hantzsch ester as hydrogen source for biomimetic transfer hydrogenation, enabled high enantioselectivity and excellent yields for a series of α,β-unsaturated cyclohexenones under mild conditions. Moreover, owing to the use of readily available and chiral pool-derived building blocks, it could be prepared in a straightforward and significantly cheaper way compared to the current state of the art.
Enantio- A nd regioselective: Ene-reductions using F420H2-dependent enzymes
Mathew, Sam,Trajkovic, Milos,Kumar, Hemant,Nguyen, Quoc-Thai,Fraaije, Marco W.
supporting information, p. 11208 - 11211 (2018/10/15)
In the past decade it has become clear that many microbes harbor enzymes that employ an unusual flavin cofactor, the F420 deazaflavin cofactor. Herein we show that F420-dependent reductases (FDRs) can successfully perform enantio-, regio- A nd chemoselective ene-reductions. For the first time, we have demonstrated that F420H2-driven reductases can be used as biocatalysts for the reduction of α,β-unsaturated ketones and aldehydes with good conversions (>99%) and excellent regioselectivities and enantiomeric excesses (>99% ee). Noteworthily, FDRs typically display an opposite enantioselectivity when compared to the well established FMN-dependent Old Yellow Enzymes (OYEs).