41597-55-1Relevant academic research and scientific papers
Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols
Macmillan, David W. C.,Oswood, Christian J.
, p. 93 - 98 (2022/01/03)
Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel
Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis-Diol Scaffolds
Laserna, Victor,Fiorani, Giulia,Whiteoak, Christopher J.,Martin, Eddy,Escudero-Adán, Eduardo,Kleij, Arjan W.
, p. 10416 - 10419 (2016/02/18)
The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using aminotriphenolate-based metal catalysts is reported. The key intermediates are cyclic carbonates, which are obtained in high yield and with high levels of diastereo- and chemoselectivity from the parent oxirane precursors and carbon dioxide. Deprotection of the carbonate structures affords synthetically useful cis-diol scaffolds with different ring sizes that incorporate various functional groups. This atom-efficient method allows the simple construction of diol synthons using inexpensive and accessible precursors and green metal catalysts and showcases the use of CO2 as a temporary protecting group. Protective Carbon: Aminotriphenolate complexes of FeIII and AlIII are highly efficient and selective catalysts for the conversion of functional (multi)cyclic oxiranes into the corresponding cis carbonates. Basic hydrolysis of the latter provides a series of useful cyclic cis-diol scaffolds in high yield. In this process, CO2 acts as both a temporary protecting group and an oxygen donor.
Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols
Cavdar, Huseyin,Saracoglu, Nurullah
experimental part, p. 985 - 989 (2009/04/07)
Sodium hydrogen sulfate (NaHSO4) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO4 gave isolable β-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction.
One-Pot and Stereospecific Synthesis of cis-1,2-Diazides via Mitsunobu Reaction of Epoxides
Goeksu, Sueleyman,Secen, Hasan,Suetbeyaz, Yasar
, p. 2373 - 2378 (2007/10/03)
Mitsunobu reaction of epoxides using hydrazoic acid, diethylazodicarboxylate, and triphenylphosphine as reagents gave the corresponding cis-1,2-diazides in moderate yield. Application of similar reaction conditions to trans-diols furnished the corresponding trans-1,2-diazides.
Chemistry of anti- and syn-1,2:3,4-Naphthalene Dioxides and Their Potential Relevance as Metabolic Intermediates
Tsang, Wing-Sum,Griffin, Gary W.,Horning, M. G.,Stillwell, W. G.
, p. 5339 - 5353 (2007/10/02)
The reactivity, site of attack, and stereochemistry of reactions of a variety of nucleophiles with the anti- and syn-1,2:3,4-naphthalene dioxides have been explored.In most cases, substituted tetrahydronaphthalene products arising through attack at the C-1 and C-4 positions in the anti mode were obtained.These isomeric dioxides provide excellent precursors for a number of difficultly accessible 1,4-disubstituted naphthalene derivatives such as 1,4-diphenoxynaphthalene and 1,4-dicyanonaphthalene.Evidence is also presented that anti-naphthalene dioxide constitutes an intermediate metabolite in the rat.
