Acid-promoted Condensation Research Articles

Lewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyrans

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyransZ. Y. Wei, D. Wang, J. S. Li, and T. H. ChanCite this: J. Org. Chem. 1989, 54, 24, 5768–5774Publication Date (Print):November 1, 1989Publication History Published online1 May 2002Published inissue 1 November 1989https://doi.org/10.1021/jo00285a025RIGHTS & PERMISSIONSArticle Views943Altmetric-Citations90LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (958 KB) Get e-Alerts Get e-Alerts

Erythro- or threo-selective aldol-type reaction via ( Z)- N, N-dimethyl- S-trimethylsilylketene S, N-acetals

N,N-Dimethylthioamides can be converted stereoselectively into ( Z)- N,N-dimethyl- S-trimethylsilylketene S,N-acetals, 2. Condensa under the influence of a catalytic amount of tetrabutylammonium fluoride affords erythro-( R ★, R ★)-β-hydroxythioamides selectively in good yields. The aldol reaction is postulated to proceed via an acyclic transition state. Lewis acid-promoted condensation of 2 with benzaldehyde on the other hand affords mainly threo-( R ★, S ★)-β-hydroxythioamides when R 1 is not too bulky.