The diastereoselective synthesis of 2, 3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles. Issue 39 (24th September 2020)

• Record Type: Journal Article
• Authors: Stead, Darren
• Is Part Of: Tetrahedron letters. Volume 61:Issue 39(2020)
• Publication Date: 2020-09-24
• Subjects: Pyrrolidine synthesis -- Cyclopropyl nitriles -- MgI2 -- Ring expansion -- Diastereoselective; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152325
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Magnesium iodide mediated cyclopropane ring expansion to give pyrrolidine products. Trans -selective 2, 3-diaryl-3-cyano-substituted pyrrolidine formation. Concise access to pyrrolidine products. Reaction of cyclopropane nitriles with tosyl aldimines. Diastereoselective diaryl-pyrrolidine formation. Abstract: The MgI2 mediated reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2, 3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans- diastereoisomer was determined to be the major product. The overall yield and diastereoselectivity of the reaction showed some sensitivity to the electronic and steric demands of the aryl cyclopropyl nitriles and the tosyl aldimines. Substitution with electron withdrawing substituents on both reacting partners proved beneficial in terms of the yield and diastereoselectivity.