652997-73-4Relevant academic research and scientific papers
A Bio-Inspired, Catalytic e → Z Isomerization of Activated Olefins
Metternich, Jan B.,Gilmour, Ryan
, p. 11254 - 11257 (2015)
Herein, Natures flavin-mediated activation of complex (poly)enes has been translated to a small molecule paradigm culminating in a highly (Z)-selective, catalytic isomerization of activated olefins using (-)-riboflavin (up to 99:1 Z/E). In contrast to the prominent Z → E isomerization of the natural system, it was possible to invert the directionality of the isomerization (E → Z) by simultaneously truncating the retinal scaffold, and introducing a third olefin substituent to augment A1,3-strain upon isomerization. Consequently, conjugation is reduced in the product chromophore leading to a substrate/product combination with discrete photophysical signatures. The operationally simple isomerization protocol has been applied to a variety of enone-derived substrates and showcased in the preparation of the medically relevant 4-substituted coumarin scaffold. A correlation of sensitizer triplet energy (ET) and reaction efficiency, together with the study of additive effects and mechanistic probes, is consistent with a triplet energy transfer mechanism.
Catalytic hydrogenation of α,β-unsaturated carboxylic acid derivatives using copper(i)/N-heterocyclic carbene complexes
Zimmermann, Birte M.,Kobosil, Sarah C. K.,Teichert, Johannes F.
supporting information, p. 2293 - 2296 (2019/02/27)
A simple and air-stable copper(i)/N-heterocyclic carbene complex enables the catalytic hydrogenation of enoates and enamides, hitherto unreactive substrates employing homogeneous copper catalysis and H2 as a terminal reducing agent. This atom economic transformation replaces commonly employed hydrosilanes and can also be carried out in an asymmetric fashion.
Stereoselective synthesis of tetrazole CB92834, a potent retinoid compound
Garipova, Goulnara,Gautier, Arnaud,Piettre, Serge R.
, p. 4755 - 4759 (2007/10/03)
An improved, convergent synthesis of CB92834 is relying on a Suzuki cross-coupling reaction and easily allows multigram-scale preparation of the compound. The approach features three highly stereoselective steps.
