Synthesis and oxidative reactivity of new chiral hypervalent iodine(V) reagents based on (S)-proline

Ladziata, Vladimir; Carlson, J.C.; Zhdankin, Viktor V.

doi:10.1016/j.tetlet.2006.06.103

Cited by 87 publications

(35 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…5 The asymmetric oxidation of sul des gave sulfoxides with moderate enantioselectivities on use of oligomeric chiral iodine(III) species 1, the structure as later proposed by Koser, 6 generated from iodosobenzene (PhIO) and tartaric anhydride derivatives. After this paper was published, several chiral hypervalent iodine reagents were developed by the groups of Koser (for oxidation of sul des), 7 Wirth (for dioxytosylation of styrene), 8 Kita (for oxidation of sul des), 9 Ochiai (for oxidative α phenylation of β ketoesters), 10 Zhdankin (for oxidative desymmetrization of vicinal diols), 11 Fujita (for oxidative cyclization of acyloxyalkenes), 12 and Birman (for oxidative dearomatization of phenols). 13 But the enantioselectivities obtained in these reactions were still moderate.…”

Section: Introductionmentioning

confidence: 99%

Conformationally-Flexible Chiral Hypervalent Organoiodine Catalysts for Enantioselective Oxidative Transformations

Uyanik¹,

Ishihara

2012

J. Synth. Org. Chem. Jpn.

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Conformationally-Flexible Chiral Hypervalent Organoiodine Catalysts for Enantioselective Oxidative Transformations

Uyanik¹,

Ishihara

2012

J. Synth. Org. Chem. Jpn.

View full text Add to dashboard Cite

“…Asymmetric oxidation of methyl p-tolyl sulfide (38) with oxidant 34 gave (R)-sulfoxide 39 with good chemical yield and moderate enantioselectivity (Scheme 5). 17 These results indicate that compounds 33 and 34 represent promising compounds for further design of chiral oxidants based on the pseudo-benziodoxazine scaffold. The initial design concept suggested that iodylarenes 33 and 34 would act as asymmetric oxidants, which was subsequently shown by the performance of a kinetic resolution experiment and asymmetric oxidations.…”

Section: Figurementioning

confidence: 86%

“…The remaining alcohol was enriched with the R-isomer with a reasonable 33% ee. 17 Similarly, chiral NIPA 33 was evaluated by oxidation of meso-diol 36 under the same reaction conditions. This oxidation led to (R)-hydroxy ketone 37 with a moderate 41% ee (Scheme 5).…”

Section: Figurementioning

confidence: 99%

N-(2-Iodylphenyl)acylamides - New Pentavalent Iodine Oxidizing Reagents

Ladziata¹,

Zhdankin²

2007

Synlett

Self Cite

View full text Add to dashboard Cite

This account describes design and synthetic utilization of new iodine(V) oxidizing reagents, N-(2-iodylphenyl)acylamides (NIPAs). NIPA reagents are soluble and stable pseudo-cyclic IBX analogues that are able to selectively oxidize either alcohols or sulfides, with the reactivity depending largely on the substitution pattern on the amido group adjacent to the iodyl moiety. A recyclable polymer-supported version of NIPA (NIPA resin) can conveniently be prepared in three simple steps. NIPA resin can effect smooth and efficient oxidation of a large variety of alcohols to the respective carbonyl compounds. Proline-based NIPA derivatives are promising chiral oxidants based on a pseudo-benziodoxazine scaffold.

show abstract

“…Enantiomers 18 were synthesized in a similar fashion, first by acylating proline under classical Schotten-Baumann conditions 33, 34 followed by amide coupling with ethyl isonipecotate (Scheme 3). Hydrolysis of the ethyl ester through a non-racemizing protocol 35 provided the carboxylic acid, and amidation with 4-(2-aminoethyl)pyridine gave the desired ( R )- and ( S )- benzoyl analogues.…”

Section: Chemistrymentioning

confidence: 99%

Discovery of anthranilamides as a novel class of inhibitors of neurotropic alphavirus replication

Barraza

Delekta

Sindac

et al. 2015

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

Neurotropic alphaviruses are debilitating pathogens that infect the central nervous system (CNS) and are transmitted to humans via mosquitoes. There exist no effective human vaccines against these viruses, underlining the need for effective antivirals, but no antiviral drugs are available for treating infection once the viruses have invaded the CNS. Previously, we reported the development of novel indole-2-carboxamide-based inhibitors of alphavirus replication that demonstrate significant reduction of viral titer and achieve measurable brain permeation in a pharmacokinetic mouse model. Herein we report our continued efforts to improve physicochemical properties predictive of in vivo blood-brain barrier (BBB) permeability through reduction of overall molecular weight, replacing the indole core with a variety of aromatic and non-aromatic monocyclics. These studies culminated in the identification of simple anthranilamides that retain excellent potency with improved metabolic stability and significantly greater aqueous solubility. Furthermore, in a live virus study, we showed that two new compounds were capable of reducing viral titer by two orders of magnitude and that these compounds likely exert their effects through a mechanism similar to that of our indole-2-carboxamide inhibitors.

show abstract

Synthesis and oxidative reactivity of new chiral hypervalent iodine(V) reagents based on (S)-proline

Cited by 87 publications

References 39 publications

Conformationally-Flexible Chiral Hypervalent Organoiodine Catalysts for Enantioselective Oxidative Transformations

Conformationally-Flexible Chiral Hypervalent Organoiodine Catalysts for Enantioselective Oxidative Transformations

N-(2-Iodylphenyl)acylamides - New Pentavalent Iodine Oxidizing Reagents

Discovery of anthranilamides as a novel class of inhibitors of neurotropic alphavirus replication

Contact Info

Product

Resources

About