Special Issue

Isao Kuwajima's Special Issues, Vol. 90, No. 1, 2015

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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.723-729
Published online: 8th August, 2014
DOI: 10.3987/COM-14-S(K)53
■ 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.

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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.730-739
Published online: 25th July, 2014
DOI: 10.3987/COM-14-S(K)54
■ 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.

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