StereoselectiveHydroxylation with Thallium(I) Acetate and Iodine:
            <i>trans</i>
            ‐ and
            <i>cis</i>
            ‐1,2‐Cyclohexanediols

Cambie, R. C.; Rutledge, P. S.

doi:10.1002/0471264180.os059.24

Cited by 2 publications

(1 citation statement)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As early as 1933, Prévost had discovered that anti ‐dihydroxylation of alkenes could be achieved using stoichiometric amounts of iodine and silver benzoate in the absence of water . In 1978, Cambie and Rutledge modified the reaction conditions for anti ‐diacetoxylation of cyclohexene by replacing the silver salt with thallium(I) acetate, which demonstrates better stability, but high toxicity …”

Section: Anti‐dioxygenation With Cyclic Cationic Intermediatesmentioning

confidence: 99%

Vicinal anti‐Dioxygenation of Alkenes

Wang

2018

Asian J Org Chem

View full text Add to dashboard Cite

Vicinal diols and their derivatives are common motifs in al arge number of biologically active compounds and are also important intermediates in organics ynthesis. To achieve these structural units in ah ighly stereoselective manner,d irect dioxygenation of simple alkene precursors has provedt ob et he most straightforward approach, and thus many practical proceduresu sing various strategies have been developed. In this Focus Review ac oncise summary of the main methods for anti-dioxygenation of olefins is presented. Scheme1.Categories of vicinal anti-dioxygenation of alkenes.[a] Prof.Scheme6.Ammonium-directed formal anti-dioxygenation as key step for the synthesis of aza-and amino sugars.Scheme7.N-Oxide-directed formal anti-dihydroxylation.Scheme8.NafionN R50-catalyzed anti-dihydroxylation.Scheme9.PTSA-catalyzed anti-dihydroxylation.Scheme14. SeO 2 -catalyzed anti-dihydroxylation.Scheme15. Diselenide-catalyzed anti-dihydroxylationo fcyclohexene.Scheme16. Chiral-diselenide-catalyzed asymmetric anti-dihydroxylation.

show abstract

Section: Anti‐dioxygenation With Cyclic Cationic Intermediatesmentioning

confidence: 99%

Vicinal anti‐Dioxygenation of Alkenes

Wang

2018

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Indispensable Applications of Electrochemical Techniques to Organic Synthetic Reactions: Enhancing Versatility and

Dick¹,

Chong²

2012

Organic Chem Curr Res

View full text Add to dashboard Cite

which is toxic, causing hyperbilirubinemia and gout [13-15]. For the palladium catalyzed heterolytic CC coupling reactions, the metal center is one of the more expensive rare earth metals [11,12], making olefin metathesis and cross coupling impractical compared to current electrochemical applications presented below. The cost for many CC coupling reactions due to these catalysts comes with a great price: not only is the opportunity cost of time and low yields involved, but health and physiological impediments must be taken into consideration along with the exorbitant expense of the transition metal itself.

show abstract

StereoselectiveHydroxylation with Thallium(I) Acetate and Iodine: trans ‐ and cis ‐1,2‐Cyclohexanediols

Abstract: Stereoselective hydroxylation with thallium(I) acetate and iodine: trans ‐ and cis ‐1,2‐cyclohexanediols solvent: 40 ml. of dried acetic acid intermediate: trans ‐1,2‐cyclohexanediol diacetate product: trans … Show more

Cited by 2 publications

References 27 publications

Vicinal anti‐Dioxygenation of Alkenes

Vicinal anti‐Dioxygenation of Alkenes

Indispensable Applications of Electrochemical Techniques to Organic Synthetic Reactions: Enhancing Versatility and

Contact Info

Product

Resources

About