Synthesis of chroman-annulated cyclopropanols via photoinduced intramolecular [2 + 1]-cycloaddition of 2-allyloxybenzaldehydes

Elvira R Zaitseva; Victoria E Opryshko; Dmitrii S Ivanov; Andrey A Mikhaylov; Alexander Yu Smirnov; Mikhail S Baranov

doi:10.1039/d3ob01520c

Synthesis of chroman-annulated cyclopropanols via photoinduced intramolecular [2 + 1]-cycloaddition of 2-allyloxybenzaldehydes

Org Biomol Chem. 2023 Nov 22;21(45):9082-9085. doi: 10.1039/d3ob01520c.

Authors

Elvira R Zaitseva¹, Victoria E Opryshko¹, Dmitrii S Ivanov¹, Andrey A Mikhaylov¹, Alexander Yu Smirnov^{1

2}, Mikhail S Baranov^{1

2}

Affiliations

¹ Institute of Bioorganic Chemistry Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997, Moscow, Russia. baranovmikes@gmail.com.
² Pirogov Russian National Research Medical University, Ostrovitianov 1, 117997, Moscow, Russia.

PMID: 37942901
DOI: 10.1039/d3ob01520c

Abstract

2-Allyloxybenzaldehydes undergo [2 + 1] cycloadditions under 365 nm LED irradiation to form the corresponding chroman-fused cyclopropanols. The reaction proceeds easily without any catalysts or additives in dimethyl sulfoxide.