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HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
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Special Issue
Isao Kuwajima's Special Issues, Vol. 90, No. 1, 2015
Published online: 8th August, 2014
■ Diquat Triflate, a Precursor of Organic Reductant
Manabu Kuroboshi,* Takashi Kondo, and Hideo Tanaka
*Division of Chemsitry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan
Abstract
Electroreduction of diquat triflate gave a potent organic reductant, which promoted reductive dimerization of aryl bromides in the presence of palladium catalysts to give the corresponding biaryl compounds.
Published online: 25th July, 2014
■ Synthesis and Crystal Structure of (4S)-4-Benzyl-3-(4,5-dimethoxy-2-methylbenzoyl)-2,2-dimethyl-1,3-oxazolidine
Maria Chrzanowska,* Zofia Meissner, Joanna M. Chrzanowska, and Andrzej K. Gzella
*Faculty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznań, Poland
Abstract
The synthesis of (4S)-4-benzyl-3-(4,5-dimethoxy-2-methylbenzoyl)-2,2-dimethyl-1,3-oxazolidine 6 was performed in 7 steps starting from veratraldehyde 7. A new oxidizing system TBHP-ebselen 12 was used for oxidation of 4,5-dimethoxy-2-methylbenzaldehyde 11 into carboxylic acid 13, being the crucial step of the synthesis. The latter was transformed first to chiral amide 14 using (S)-phenylalaninol and then cyclised to oxazolidine 6. The spatial structure and the absolute configuration of the latter one was confirmed by X-ray study.