Diastereodivergent and Enantioselective Organocatalytic Synthesis of Spiro-Fused Coumarins via [4+2] Cycloadditions

Organic Letters 2026 Open access

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Authors: Raquel Hidalgo-León, José Enrique Trujillo-Sierra, José M. Sansano, Fernando P. Cossío, Abel de Cozar, María de Gracia Retamosa
DOI: 10.1021/acs.orglett.5c05358
Cited by: 3
References: 51

Abstract

High Resolution Image Download MS PowerPoint Slide A highly enantioselective, organocatalytic, diastereodivergent synthesis of spiro-fused coumarin derivatives via trienamine-mediated Diels–Alder reactions with cyclic 2,5-dienones is reported. Using a cinchonidine-based primary amine and either p -methylbenzoic acid or triethylamine enables reversible diastereoselectivity, providing complementary enantioenriched diastereoisomers. The influence of electron-withdrawing groups at C3 of coumarins is delineated, revealing distinct reactivity patterns. Computational studies provide insight into the mechanism and additive-controlled diastereodivergence.

Fields of Study & Subjects

Cyclopropane Reaction Mechanisms Asymmetric Synthesis and Catalysis Radical Photochemical Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
6
Pages
2069–2075
Publication date
29 January 2026
Language
EN