Recent Developments in Asymmetric Hetero-Diels-Alder Reactions of Dithioesters

Recent studies dealing with asymmetric thia-Diels-Alder reactions of dithioesters as heterodienophiles are described. A diastereoselective version involving new chiral dithioesters and the first example of a catalytic enantioselective version are described. The absolute stereochemistry of the cycloa...

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Published inPhosphorus, sulfur, and silicon and the related elements Vol. 188; no. 4; pp. 349 - 355
Main Authors Dentel, Hélène, Gulea, Mihaela
Format Journal Article
LanguageEnglish
Published Abingdon Taylor & Francis Group 01.04.2013
Taylor & Francis Ltd
Subjects
Asymmetric hetero-Diels-Alder reaction
chiral dithioester
Cu(II)/bis(oxazoline) complex
stereochemical models
thia-Diels-Alder reaction
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Summary:Recent studies dealing with asymmetric thia-Diels-Alder reactions of dithioesters as heterodienophiles are described. A diastereoselective version involving new chiral dithioesters and the first example of a catalytic enantioselective version are described. The absolute stereochemistry of the cycloadducts was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction observed experimentally, stereochemical models for Cu(II)/BOX/dithioester complexes are proposed.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2012.729113