Organocatalytic Michael addition of indanone carboxylates to vinyl selenone for the asymmetric synthesis of polycyclic pyrrolidines

The effect of mobile phase composition in the enantioseparation of pharmaceutically relevant compounds with polysaccharide‐based stationary phases

“…Compounds 1–5 (Díaz‐Gavilán et al ., ; Conejo‐García et al ., ), 6 , 7 (Marinozzi et al ., ), 8 (Sternativo et al ., ), 9 and 10 (Gioiello et al ., ; Fig. ) were synthesized according to reported procedures.…”

“…The group of selected analytes comprised: five purine derivatives ( 1–5 ) with relevant activity against human breast cancer cell line MCF‐7 (Díaz‐Gavilán et al ., ; Conejo‐García et al ., ; Natalini et al ., ); two nonsteroidal agonists of the Farnesoid X Receptor ( 6 , 7 ) (Marinozzi et al ., ), a promising target for the treatment of a variety of metabolic disorders, including hyperlipidemia, cholelithiasis, cholestasis and diabetes mellitus; a conformationally restricted β‐amino acid ( 8 ) to be evaluated as angiotensin converting enzyme inhibitor (Sternativo et al ., ); and the E‐ and Z‐guggulsterones ( 9 , 10 ), especially known for their ability to reduce lipid and cholesterol levels (Gioiello et al ., ), for their utility in the treatment of various cardiovascular diseases, and to be endowed with anti‐neoplastic properties.…”

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

“…The use of pseudo-enantiomeric catalysts Ophenantryl C6′OH-QD and C6′OH-Q, having opposite configurations at C8 and C9, provided spirolactones with comparable yields and enantiomeric excesses, but opposite enantioselectivity (Scheme 18). Organocatalyzed Michael-initiated cyclizations for the enantioselective synthesis of polycyclic compounds, such as spirolactones [49] and β-aminoesters [50] with a tetrahydroindeno [1,2-b]pyrrole core, were also developed by the same authors. In these reactions, the selenonyl group also acts as a traceless agent able to activate and control the addition step.…”

“…Organocatalyzed Michael-initiated cyclizations for the enantioselective synthesis of polycyclic compounds, such as spirolactones [ 49 ] and β-aminoesters [ 50 ] with a tetrahydroindeno[1,2- b ]pyrrole core, were also developed by the same authors. In these reactions, the selenonyl group also acts as a traceless agent able to activate and control the addition step.…”

An eco-friendly three-component regio- and stereoselective synthesis of highly functionalized dihydroindeno[1,2-b]pyrroles under grinding

“…It is pertinent to note that there are only a few reports available on the synthesis of the oxoindeno- [1,2-b]pyrrole ring system. [28][29][30][31] These methods, however, suffer from one or more disadvantages such as long reaction times, low yield, need for column chromatographic purification, etc. This reaction could also be successfully extended to aliphatic amines, viz.…”