Universität zu Köln

Lefarth, Jens ORCID: 0000-0003-3234-2032, Neudoerfl, Jorg and Griesbeck, Axel G. (2021). 9a-Phenyl-2,3,3a,3b,9a,9b-hexahydro-4H-furo[3 ',2 ':3,4]cyclobuta-[1,2-b]chromen-4-one: A Flavone-Based [2. Molbank, 2021 (3). BASEL: MDPI. ISSN 1422-8599

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Abstract

The intermolecular [2 + 2]-photocycloaddition of the parent flavone molecule (4) as the triplet energy-accepting species and the electron-rich alkene 2, 3-dihydrofuran (5) was performed by visible-light-mediated triplet-sensitization with an iridium-based organometallic sensitizer. The reaction proceeds with high diastereo- and regioselectivity (>98:2 for the regiochemical orientation and with 95% d.s.). In contrast to numerous other ene/enone combinations that are described in the literature and were also performed by us, the reaction between 4 and 5 almost solely afforded the cis-syn-cis cyclobutane 6, whereas analogous conjugated six- and five-membered cycloalkenones preferentially react to cis-anti-cis cyclobutanes or a mixture of both diastereoisomers (e.g., for the cyclohexanone-derived example 9).

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Lefarth, Jens UNSPECIFIED orcid.org/0000-0003-3234-2032 UNSPECIFIED Neudoerfl, Jorg UNSPECIFIED UNSPECIFIED UNSPECIFIED Griesbeck, Axel G. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-563065
DOI:	10.3390/M1256
Journal or Publication Title:	Molbank
Volume:	2021
Number:	3
Date:	2021
Publisher:	MDPI
Place of Publication:	BASEL
ISSN:	1422-8599
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language VISIBLE-LIGHT; TRIPLET-STATE; PHOTOCYCLOADDITION REACTIONS; PHOTOCHEMICAL-REACTIONS; DERIVATIVES; CHALCONES Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/56306