Advances in organocatalytic asymmetric reactions of vinylindoles: powerful access to enantioenriched indole derivatives

Abstract

Enantioenriched indole derivatives are widely found in natural products, pharmaceuticals and bioactive compounds. Therefore, developing efficient methods for the synthesis of enantioenriched indole derivatives has become an important goal in...

Atroposelective Construction of Axially Chiral Alkene‐Indole Scaffolds via Catalytic Enantioselective Addition Reaction of 3‐Alkynyl‐2‐indolylmethanols†

“…In recent years, catalytic enantioselective construction of indole-based axially chiral frameworks has become an emerging area [16] because indole belongs to five-membered heteroaryls with unique properties. [17] Synthetic chemists have designed innovative strategies for constructing different axially chiral arylindoles such as N-arylindoles, [18] 3-arylindoles, [19] 2-arylindoles [20] and bisindoles. [21] Based on these works, we conceived if an alkenyl group was introduced to the indole moiety, axially chiral alkene-indoles as a new class of atropoisomeric indole-based scaffolds would be generated (Scheme 2a).…”

Regiodivergent Organocatalytic Reactions

“…The utilization of organocatalysts has garnered interest because they are robust, inexpensive, environmentally benign, and easily recoverable, among other advantageous characteristics. Moreover, the use of chiral organic molecules as catalysts enables the synthesis of highly enantio-and diastereomeric pure products, which are of great importance in medicinal and pharmaceutical chemistry [15][16][17][18].…”

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

“…Because indoles are readily available materials, the direct extension of indoles to carbazole skeletons has a great advantage [19][20][21][22][23][24][25][26][27]. Therefore, the Diels-Alder reaction of activated 2-vinylindolines or 3-vinylindolines with diverse dienophiles has become the most attractive strategy for the synthesis of carbazole deriv- atives [28][29][30][31][32][33][34][35][36][37][38][39][40]. In recent years, by using the one-pot domino synthetic strategy of in situ-generated 2-vinyl-or 3-vinylindolines and sequential Diels-Alder reaction with activated dienophiles, we have successfully developed several efficient synthetic protocols for diversely functionalized tetrahydrocarbazoles and the corresponding carbazole derivatives [41][42][43][44][45][46][47].…”