Iodine(III)-Promoted Ring Expansion of 1-Vinylcycloalkanol Derivatives: A Metal-Free Approach toward Seven-Membered Rings †
Instituto de Química, Universidade de São Paulo, Avenida Professor Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil.Organic Letters (Impact Factor: 6.36). 04/2008; 10(5):1017-20. DOI: 10.1021/ol800048f
A versatile and metal-free approach for the synthesis of molecules bearing seven- and eight-membered rings is described. The strategy is based on the ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). The reaction condition can be easily adjusted to give seven-membered rings bearing different functional groups. A route to medium-ring lactones was also developed.
- ChemInform 08/2008; 39(32). DOI:10.1002/chin.200832063
Article: Chemistry of Polyvalent Iodine[Show abstract] [Hide abstract]
ABSTRACT: The chemistry of Polyvalent Iodine ranging from structure and bonding, preparation, compounds to the various computational and experimental structures was studied. The main purpose of this study is to summarize the data that appeared in the literature following publication of some previous reviews, and was organized according to the classes of organic polyvalent iodine compounds, by emphasizing their synthetic application. The number of X-ray crystal structures have also been reported for the main classes of organic polyvalent iodine compounds. Several compounds as Iodine (III) compounds, Iodosylarenes, and Fluorides and chlorides were also investigated. The Iodine (III)compound is exhibiting growing interests mainly due to their useful oxidizing properties, combined with their bening environmental character and commercial availability.Chemical Reviews 12/2008; 108(12):5299-358. DOI:10.1021/cr800332c · 46.57 Impact Factor
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ABSTRACT: A set of enantiopure carbohydrate mimetics has been synthesized via Lewis acid promoted cyclization of 1,3-dioxolanyl-substituted enol ethers as a crucial new step providing highly functionalized 3,6-dihydro-2H-pyran derivatives. The flexible approach starting from glyceraldehyde-derived nitrone is comprised of only six simple steps smoothly allowing synthetic modifications at the different stages of the sequence. All reactions proceeded with good to excellent stereocontrol and can be performed with either of the two enantiomers.Organic Letters 11/2009; 11(23):5534-7. DOI:10.1021/ol902354f · 6.36 Impact Factor
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