Synthesis of spirocyclopentene-indolines by intramolecular alkylidine insertion reactions

Palladium‐Catalyzed Cascade sp2 C−H Functionalization/Intramolecular Asymmetric Allylation: From Aryl Ureas and 1,3‐Dienes to Chiral Indolines

“…The absolute configuration of 6 could be determined by comparison of the optical rotation data with literature reports . Further, according to previous report, the electron‐deficient C−C double bond could also undergo Michael addition reactions to further build up molecular complexity …”

“…[8] Further,a ccording to previous report, the electron-deficient CÀCd ouble bond could also undergo Michael addition reactions to further build up molecular complexity. [17] In conclusion, we reported achiral Pd II -catalyzed cascade sp 2 C À Hf unctionalization/intramolecular asymmetric allylation reaction. Anew chiral sulfoxide-oxazoline (SOX) ligand bearing single chiral center on the sulfur was identified as the optimal ligand for the reaction, being efficient both in the CÀ Hc leavage step and the stereo-control of the allylation step.…”

Total syntheses of pyrroloazocine indole alkaloids: challenges and reaction discovery

“…The Diels-Alder reaction between an indoline-containing diene and a dienophile has also been widely used in the synthesis of indole alkaloids 23 (Scheme 5). An alternative approach to spiro[indoline-cyclohexanes] is based on C6 ring-closing transformations (Scheme 3d), such as aldol-type reactions, 24,25 olefin metathesis, 26 and Dieckmann condensation. 27,28 The last two approaches were developed by the group of Nishida in the course of the total synthesis of lundurines.…”