Details

Autor(en) / Beteiligte

• Quezada, Víctor
• Castroagudín, Mariña
• Verdugo, Felipe
• Ortiz, Sergio
• Zaragoza, Guillermo
• Nachtigall, Fabiane M
• Reis, Francisco A A
• Castro-Alvarez, Alejandro
• Santos, Leonardo S
• Nelson, Ronald

Titel

Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor-Acceptor Cyclopropanes

Ist Teil von

• Molecules (Basel, Switzerland), 2024-04, Vol.29 (7), p.1604

Ort / Verlag

Switzerland: MDPI AG

Erscheinungsjahr

2024

Link zum Volltext

Quelle

EZB Free E-Journals

Beschreibungen/Notizen

• This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between -substituted indoles and donor-acceptor cyclopropanes to synthesize cyclopenta[ ]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and 8.6:1 with complete regioselectivity. The substrate scope showed high tolerance to various substituted indoles and cyclopropanes, resulting in the synthesis of six new cyclopenta[ ]indoles and the isolation of five derivatives previously reported in the literature. In addition, a mechanistic proposal for the reaction was studied through online reaction monitoring by ESI-MS, allowing for the identification of the reactive intermediates in the Ni(II) catalyzed process. X-ray crystallography confirmed the structure and relative endo stereochemistry of the products. This method enables the fast and efficient construction of fused indolines from readily accessible starting materials.