Metallic Base-Induced Cycloadditions ofN-(1-Cyanoalkyl)imines viaN-Metalated Azomethine Ylides: Enhanced Reactivity and High Regio- and Stereoselectivity

Studies of Regio- and Stereoselectivity

Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Azomethine Ylides for Biology-Oriented Synthesis

Cycloaddition reactions are among the most powerful methods for the synthesis of complex compounds. In particular, the development and application of the 1,3-dipolar cycloaddition, an important member of this reaction class, has grown immensely due to its powerful ability to efficiently build various five-membered heterocycles. Azomethine ylides are commonly used as dipoles for the synthesis of...

Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters†

Catalytic, enantioselective [3 + 2] cycloadditions of azomethine ylides derived from alanine imino esters with 3-nitroindoles are reported. The dearomative cycloaddition reactions occur in the presence of a catalyst generated in situ from Cu(OTf)2 and (R)-Difluorphos to form exo’-pyrroloindoline cycloadducts and establish four contiguous stereogenic centers, two of which are fully substituted. ...

The Bonding Situation in Metalated Ylides

Quantum chemical calculations have been carried out to study the electronic structure of metalated ylides particularly in comparison to their neutral analogues, the bisylides. A series of compounds of the general composition Ph3 P-C-L with L being either a neutral or an anionic ligand were analyzed and the impact of the nature of the substituent L and the total charge on the electronics and bon...

Copper(II)-catalyzed exo and enantioselective cycloadditions of azomethine imines.

A strategy for exo and enantioselective 1,3-dipolar cycloaddition of azomethine imines to 2-acryloyl-3-pyrazolidinone is described. The corresponding cycloadducts are isolated with high diastereoselectivities (up to >96:4 exo/endo) and enantioselectivities (up to 98% ee).