Tandem reactions of Pd‐catalyzed cross‐coupling of 3‐(2‐isocyanoethyl)indoles with diazoacetates and subsequent spirocyclization/Mannich‐type reaction have been developed to assemble polycyclic spiroindoline skeletons. Formation of spiroindolenines has been proven as the crucial step for the following Mannich‐type cyclization reaction. Accordingly, a novel approach on chiral phosphoric acid catalyzed Mannich‐type cyclization toward the formation of diastereomerically and enantiomerically enriched pentacyclic spiroindolines has been established. Moreover, the products of the reaction are versatile building blocks in synthetic chemistry, as demonstrated by the synthesis of the key framework of aspidosperma and kopsia alkaloids.
Iridium-Catalyzed C-3 Allylation of Indoles with Allylic Alcohols Promoted by a Broensted Acid. -Attempts upon an asymmetric allylation using a chiral bisoxazoline ligand provide only racemic product. -(CHEN, S.-J.; LU, G.-P.; CAI*, C.; Synthesis 46 (2014) 13, 1717-1724, http://dx.
Iridium-Catalyzed Methylation of Indoles and Pyrroles Using Methanol as Feedstock. -While indoles are regioselectively mono-methylated at C-3, pyrroles give mixtures of mono-, di-, and (in the case of unsubstituted pyrrole) polymethylated products. N-methylindole does not react. -(CHEN, S.-J.; LU, G.-P.; CAI*, C.; RSC Adv. 5 (2015) 86, 70329-70332, http://dx.
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