Universität zu Köln

Weber, Anja, Breugst, Martin ORCID: 0000-0003-0950-8858 and Pietruszka, Joerg (2020). Experimental and Computational Investigations of the Reactions between alpha,beta-Unsaturated Lactones and 1,3-Dienes by Cooperative Lewis Acid/Bronsted Acid Catalysis. Angew. Chem.-Int. Edit., 59 (42). S. 18709 - 18717. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

The reactions of alpha,beta-unsaturated delta-lactones with activated dienes such as 1,3-dimethoxy-1-[(trimethylsilyl)oxy]-1,3-butadiene (Brassard's diene) are barely known in literature and show high potential for the synthesis of isocoumarin moieties. An in-depth investigation of this reaction proved a stepwise mechanism via the vinylogous Michael-products. Subsequent cyclisation and oxidation by LHMDS and DDQ, respectively, provided six mellein derivatives (30-84 %) and four angelicoin derivatives (40-78 %) over three steps. DFT-calculations provide insights into the reaction mechanism and support the theory of a stepwise reaction.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Weber, Anja UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Pietruszka, Joerg UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-323084
DOI:	10.1002/anie.202008365
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	59
Number:	42
Page Range:	S. 18709 - 18717
Date:	2020
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language DIELS-ALDER REACTION; STRUCTURE ELUCIDATION; ONE-POT; PSYMBERIN; PEDERIN; CLADOSPORIN; DERIVATIVES; KETONES; FUNGI Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/32308