Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Abstract

Ring opening of donor-acceptor cyclopropanes with variousN-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor-acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.

Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes

“…It occurs smoothly both with 1,3‐zwitterions and 1,2‐zwitterions generated from DACs. By using these reactions, it is possible to create complex heterocyclic systems that find use as biologically active compounds and in total syntheses of natural compounds …”

Reaction of 3-Oxa-2-oxobicyclo[4.2.0]oct-4-ene-1-carboxylate with Dimethylsulfoxonium Methylide

“…[1][2][3][4][5][6][7][8][9][10] Cycloalkanes play an important role in the field of organic synthesis as they can take part in various types of reactions. [11][12][13][14][15][16][17][18][19][20][21][22] These compounds are highly reactive toward ring-opening reactions. The high reactivities can be attributed to the angle and torsional strains.…”

Donor‐Acceptor Cyclopropanes in the Synthesis of Carbocycles

“…With all these achievements in mind, Werz and co‐authors have characterized this period as “A new golden age for donor‐acceptor cyclopropanes” . The large interest to the chemistry of D‐A cyclopropanes and significant contributions to various areas of their reactivity have been demonstrated by multiple reviews published in last decade –…”