New Diels-Alder Reactions with Vinylindoles: A Regio- and Stereocontrolled Access to Annellated Indoles and Derivatives

Abstract

New struotilral aspects of vinylindoles for predicting the outcome of Diels-Alder reactions are presented for the first time. Novel, mostly regio-and stereoselective oycloaddition reactions with 3-and 2vinylindoles are described briefly and, in some cases, new applications for the syntheses of alkaloids are discussed.

Vinylpyrroles

“…599 and references cited therein). As a consequence of their 4n-donor reactivity, C-vinylindoles (E,,,, ca.…”

Chiral Brønsted Acid Catalyzed Stereoselective Addition of Azlactones to 3‐Vinylindoles for Facile Access to Enantioenriched Tryptophan Derivatives

“…3-Vinylindoles have been employed as the diene component in enantioselective (hetero) Diels-Alder reactions, which give rise to enantioenriched polycyclic indoles. [12,13] However, to our knowledge, they have never been utilized in enantioselective addition reactions. Our method provides an alternative approach to enantioenriched indoles with a chiral side-chain at the 3position.…”

Synthesis of a new series of 2-vinylindoles and their cycloaddition reactivity

“…For instance, the cycloaddition of vinylindoles with carbon-and heteroatomic dienophiles provides indole alkaloids, carbazoles, [b]annelated indole derivatives. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Prudhomme et al synthesized structural analogs of granulatimide (1) and investigated their biological activities as new checkpoint kinase 1 inhibitors (Fig. 1).…”