[reaction: see text] 12-Oxatricyclo[6.3.1.0(2,7)]dodecanes can be efficiently synthesized in a stereoselective manner by Prins-pinacol reactions. By biasing the transition state of the Prins cyclization, it is possible to access either stereoisomer of this oxatricyclic ring system.
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http://dx.doi.org/10.1021/ol0482745 | DOI Listing |
Chemistry
December 2016
Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India.
Top Curr Chem
December 2016
Laboratoire de Méthodologies et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada.
This chapter describes advances in hypervalent iodine(III)-induced rearrangements reported between 2004 and 2015, beginning with Hofmann-type rearrangements and aliphatic aryl transpositions. In both reactions the iodine(III) reagent may be off-the-shelf or catalytically generated in situ. A number of stereoselective transformations are discussed, followed by transpositions triggered through phenol dearomatization, including Wagner-Meerwein-type rearrangements, Prins-pinacol transpositions, and a tandem polycylization-pinacol process.
View Article and Find Full Text PDFOrg Biomol Chem
August 2015
Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.
A wide array of aldehydes undergo smooth cross-coupling with 3-hydroxy-3-(4-hydroxybut-1-en-2-yl)-1-methylindolin-2-one in the presence of 10 mol% BF3·OEt2 at 0 °C in dichloromethane to afford the corresponding 2,3,5,6-tetrahydro-1'H-spiro[pyran-4,4'-quinoline]-2',3'-dione derivatives in good yields with excellent diastereoselectivity. This is the first report on the synthesis of tetrahydro-1'H-spiro[pyran-4,4'-quinoline]-2',3'-dione scaffolds through a cascade of Prins/pinacol reactions.
View Article and Find Full Text PDFOrg Biomol Chem
October 2014
Natural Product Chemistry, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500607, India.
A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a cascade of Prins/pinacol rearrangement.
View Article and Find Full Text PDFJ Org Chem
January 2010
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Polycyclic products containing the 12-oxatricyclo[6.3.1.
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