Visible-light-driven enantioselective intermolecular [2 + 2] photocyclization utilizing bathochromic excitation mediated by a chiral phosphoric acid

文献情報

出版日 2023-11-10

DOI 10.1039/D3OB01425H

インパクトファクター 3.876

著者

Tatsuhiro Uchikura, Kazuki Takahashi, Tatsushi Oishi, Takahiko Akiyama

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要旨

We report herein an enantioselective intermolecular [2 + 2] photocyclization of alkenyl 2-pyrrolyl ketones using the bathochromic shift mediated by a chiral phosphoric acid. This synthetic method provides access to cyclobutanes with up to 98% ee. According to the UV–Vis spectra, the bathochromic effect was observed by mixing alkenyl 2-pyrrolyl ketones and a chiral phosphoric acid. A non-linear correlation was observed between the ee of the catalyst and the ee of the cycloadduct, suggesting that both substrates bind to the chiral phosphoric acid and form a dimer complex before photocycloaddition.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Visible-light-driven enantioselective intermolecular [2 + 2] photocyclization utilizing bathochromic excitation mediated by a chiral phosphoric acid

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