Synthetic methods for azaheterocyclic phosphonates and their biological activity.

Advances in dearomatization strategies of indoles

This Review provides an in-depth account of the synthesis of spirocyclic indolenines. Over the last 77 years, a wide array of diverse synthetic methods has been developed in order to generate these synthetically useful and biologically important spirocyclic scaffolds. The main synthetic strategies discussed are grouped into three main categories, namely interrupted Fischer indolisations, dearomatisation reactions of indoles and condensation reactions. The historical background, common synthetic challenges, current state-of-the-art and future perspectives of this field are examined.

Synthesis of Spirocyclic Indolenines

Radicals in organic synthesis: part 2

Copper Catalyzed Atom Transfer Radical Cyclization Reactions

One‐Pot Tandem 1,4–1,2‐Addition of Phosphites to α,β‐Unsaturated Imines for the Synthesis of Glutamic Acid Analogues

Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization

Synthesis of 5-methoxylated 3-pyrrolin-2-ones via the rearrangement of chlorinated pyrrolidin-2-ones

Trialkyl phosphites were evaluated for addition reactions to α,β-unsaturated imines. An acidic medium is required to allow consecutive 1,4- and 1,2-addition to occur. In this manner, 3-phosphonyl-1-aminophosphonates, phosphonic acid analogues of glutamate, are obtained in good yields (32−90%). The reaction is mainly influenced by the steric bulk of the nitrogen substituent:  less steric N-substituents lead to better yields of the tandem adducts.

Tandem addition of trialkyl phosphites to α,β-unsaturated imines : A comparison with silylated phosphites

A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones

Ellen Van Meenen

Papers

One‐Pot Tandem 1,4–1,2‐Addition of Phosphites to α,β‐Unsaturated Imines for the Synthesis of Glutamic Acid Analogues

Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization

Synthesis of 5-methoxylated 3-pyrrolin-2-ones via the rearrangement of chlorinated pyrrolidin-2-ones

Tandem addition of trialkyl phosphites to α,β-unsaturated imines : A comparison with silylated phosphites

A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones