Year: 2022
Type: article
Abstract: Detailed herein is the development of a photochemical intermolecular formal [3+2] cycloaddition between cyclopropylimines and substituted alkenes to generate cyclopentylimines. The Schiff base auxiliary of the cyclopropylimine was designed to enable a masked N-centered radical approach in which the requisite open-shell character was achieved upon excitation with violet light. The cycloaddition products were directly converted to N-functionalized aminocyclopentanes via N-acylation and solvolysis, thus offering a three-step, one-pot procedure for the production of diversely-substituted aminocyclopentanes. The photochemical component of this reaction sequence was demonstrated to operate in continuous flow and was amenable to gram-scale production.
Source: Organic Letters
Authors: James L. Collins, Daryl Staveness, Madison J. Sowden, Corey R. J. Stephenson
Institution: University of Michigan
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Photochemical synthesis of bioactive molecules, G1338508527, G1486032164, G1545487688, G2341277371, G3385014294, G4241918764, Improving Metabolic Stability Profiles in Kinase Inhibitor Development Through the Use of 1-Aminonorbornanes as Aniline Bioisosteres, G5162923015, Free radical strategies for bioactive molecule synthesis, G6822692499
OpenAlex ID: W4282933903