Synthesis of Tetrahydro‑1<i>H</i>‑indeno[1,2‑<i>b</i>]pyridine via Cascade Cyclization and Friedel–Crafts Reaction

A convenient protocol has been established for the synthesis of 1-tosyl-2,3,4,5-tetrahydro-1<i>H</i>-indeno­[1,2-<i>b</i>]­pyridine via cascade cyclization and Friedel–Crafts reaction of 4-methyl-<i>N</i>-(pent-4-yn-1-yl)­benzenesulfonamides and aldehydes in good yields. The methodology has been used for the total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1<i>H</i>-indeno­[1,2-<i>b</i>]­pyridine

Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via a Tandem Aza Prins-Ritter/Friedel–Crafts Type Reaction of Endocyclic <i>N</i>‑Acyliminium Ions

A simple protocol is described for the synthesis of amido and phenyl hexahydroindolizin-3­(2<i>H</i>)-one, hexahydro-1<i>H</i>-quinolizin-4­(6<i>H</i>)-one, and 1,3,4,10<i>b</i>-tetrahydropyrido­[2,1<i>-a</i>]­isoindol-6­(2<i>H</i>)-one derivatives via endo-trig (aza-Prins type) cyclization followed by an intermolecular Ritter/Friedel–Crafts reaction of cyclic <i>N</i>-acyliminium ions, which are derived from the boron trifluoride etherate treatment of regioselectively reduced <i>N</i>-homoallyl imides. The reactions are highly diastereoselective with excellent yields

Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total Asymmetric Synthesis of (+)-Civet Cat Compound

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) can be efficiently used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2<i>H</i>-pyran-2-acetates stereo- and regioselectively in good yields. The methodology was used for the total synthesis of natural product (+)-civet

Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via a Tandem Aza Prins-Ritter/Friedel–Crafts Type Reaction of Endocyclic <i>N</i>‑Acyliminium Ions

A simple protocol is described for the synthesis of amido and phenyl hexahydroindolizin-3­(2<i>H</i>)-one, hexahydro-1<i>H</i>-quinolizin-4­(6<i>H</i>)-one, and 1,3,4,10<i>b</i>-tetrahydropyrido­[2,1<i>-a</i>]­isoindol-6­(2<i>H</i>)-one derivatives via endo-trig (aza-Prins type) cyclization followed by an intermolecular Ritter/Friedel–Crafts reaction of cyclic <i>N</i>-acyliminium ions, which are derived from the boron trifluoride etherate treatment of regioselectively reduced <i>N</i>-homoallyl imides. The reactions are highly diastereoselective with excellent yields

Synthesis of Tetrahydro‑1<i>H</i>‑indeno[1,2‑<i>b</i>]pyridine via Cascade Cyclization and Friedel–Crafts Reaction

A convenient protocol has been established for the synthesis of 1-tosyl-2,3,4,5-tetrahydro-1<i>H</i>-indeno­[1,2-<i>b</i>]­pyridine via cascade cyclization and Friedel–Crafts reaction of 4-methyl-<i>N</i>-(pent-4-yn-1-yl)­benzenesulfonamides and aldehydes in good yields. The methodology has been used for the total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1<i>H</i>-indeno­[1,2-<i>b</i>]­pyridine

Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total Asymmetric Synthesis of (+)-Civet Cat Compound

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) can be efficiently used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2<i>H</i>-pyran-2-acetates stereo- and regioselectively in good yields. The methodology was used for the total synthesis of natural product (+)-civet

Synthesis of Tetrahydro‑1<i>H</i>‑indeno[1,2‑<i>b</i>]pyridine via Cascade Cyclization and Friedel–Crafts Reaction

A convenient protocol has been established for the synthesis of 1-tosyl-2,3,4,5-tetrahydro-1<i>H</i>-indeno­[1,2-<i>b</i>]­pyridine via cascade cyclization and Friedel–Crafts reaction of 4-methyl-<i>N</i>-(pent-4-yn-1-yl)­benzenesulfonamides and aldehydes in good yields. The methodology has been used for the total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1<i>H</i>-indeno­[1,2-<i>b</i>]­pyridine