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Stereoselective Visible‐Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings
Author(s) -
Medici Fabrizio,
Resta Simonetta,
Presenti Piero,
Caruso Lucia,
Puglisi Alessandra,
Raimondi Laura,
Rossi Sergio,
Benaglia Maurizio
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100397
Subject(s) - cyclopentane , stereoselectivity , chemistry , catalysis , enantiomeric excess , enantiomer , combinatorial chemistry , enantioselective synthesis , aryl , organic chemistry , alkyl
Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal‐free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in‐flow synthesis of enantiomerically enriched functionalized cyclopentane rings, taking advantage of the flow reactors technology. The use of a chiral auxiliary on the bisenone to be cyclized offers a straightforward and convenient option to exert a stereocontrol on the light‐driven cyclization. By exploiting Evans’ oxazolidinones, the stereoselective light‐driven cyclization affords, after the removal of the chiral auxiliary, a functionalized 1,2‐ trans cyclopentane ring in up to 83/17 enantiomeric ratio. When the reaction was performed in continuo, in a homemade coil photoreactor, high yields were observed. The cyclization was also successfully realized in a 3D‐printed mesoreactor, without any change in the diastereoseletctivity of the process.