Indium-mediated Reformatsky reaction on lactones: preparation of 2-deoxy-2,2′-dimethyl-3-ulosonic acids

Soengas, Raquel G.

doi:10.1016/j.tetlet.2009.10.092

Cited by 17 publications

(6 citation statements)

References 30 publications

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“…Given that ring-opening of β-lactol in this model system is such an exergonic process, it is unlikely that β-lactols (i.e., oxetanes with free 2-hydroxy group) exist in any detectable concentration. For example, small organic molecules and sugars, postulated to exist in a β-lactol form based on the absence of the carbonyl peak in 13 C NMR, could be dimeric 2,5-dihydroxy-1,4-dioxanes. Fluorinated β-lactols could be the dimeric 1,4-dioxanes or simply carbonyl hydrates, i.e., gem -diols.…”

Section: Resultsmentioning

confidence: 58%

Natural Products Containing the Oxetane and Related Moieties Present Additional Challenges for Structure Elucidation: A DU8+ Computational Case Study

2019

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Analysis of published NMR data for natural products containing the oxetane moiety, with the help of a recently developed parametric/DFT hybrid computational method DU8+, has revealed that oxetanes and related compounds constitute yet another significant challenge in structure elucidation and stereochemistry assignment, as more than 30 structures required revision. The most common pitfalls are discussed, and revised structures are suggested for 26 natural products.

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Section: Resultsmentioning

confidence: 58%

Natural Products Containing the Oxetane and Related Moieties Present Additional Challenges for Structure Elucidation: A DU8+ Computational Case Study

2019

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“…Lactones can also be modified through an indium-mediated Reformatsky reaction with ethyl α-bromoisobutyrate under ultrasonication, leading to the corresponding ketals in satisfactory yields (Scheme ). The protocol was also applicable to the functionalization of sugar lactones, giving rise to ulosonic acid esters with remarkable chemoselectivity. − …”

Section: Indium Enolatementioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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allylation performed in aqueous media, an efficient synthesis of highly functionalized lactones was realized in good yields (64− 77%, Scheme 29). 238 However, the chirality installed during the first step almost had no influence on the second step, thus resulting in poor diastereoselectivity in the subsequent allylation reaction (1:1−2:1 dr).In situ formation of aldehyde from the oxidation of alcohol followed by one-pot indium-mediated allylation also provides an alternative method for the synthesis of homoallylic alcohol. Recently, Yadav and co-workers developed such a one-pot sequence by using chloramines-T (sodium salt of Nchlorotosylamide) as oxidant in the presence of a catalytic amount of FeCl 3 in CH 2 Cl 2 , giving rise to homoallylic alcohols in good to excellent yields (Scheme 30). 239 It is noteworthy that the generated byproduct of TsNH 2 (from the reduction of chloramines-T) may react with the in situ-formed aldehydes to give intermediates of N-tosylimines in the presence of 4 Å molecular sieve under refluxing; the thus-formed N-tosylimines subsequently underwent one-pot indium-mediated allylation to produce homoallylic amines in 60−80% yields. Later, a similar one-pot, two-step sequence for the synthesis of homoallylic alcohols via a galactose oxidase-mediated chemo-enzymatic oxidation of benzyl and cinnamyl alcohols to the corresponding Scheme 23 Scheme 24 Scheme 25 Scheme 26 Scheme 27 Scheme 28 Scheme 29 Scheme 30 Chemical Reviews Review dx.

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“…Ultrasonic irradiation has previously proven useful in indium-mediated protocols. 5 As a result, the reaction was also carried out with the vessel immersed in an ultrasonic cleaning bath, a process that gave the hydroxymethylated esters in better yields. .…”

Section: Scheme 1 Indium-mediated Reaction Of Ethyl Bromoisobutyrate mentioning

confidence: 99%

Convenient Procedure for the Indium-Mediated Hydroxymethylation of Active Bromo Compounds: Transformation of Ketones into α-Hydroxymethyl Nitroalkanes

Soengas¹,

Estévez²

2010

Synlett

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I n d i u m -M e d i a t e d H y d r o x y m e t h y l a t i o n o f A c t i v e B r o m o C o m p o u n d sAbstract: A very simple, safe and powerful method for the hydroxymethylation of 2-bromoesters and lactones under anhydrous conditions that avoids the use of gaseous formaldehyde is described. Moreover, under these conditions, bromonitroalkanes were converted into the corresponding a-monohydroxymethylated nitroalkanes, which are precursors of the corresponding a-amino acids. Considering the easy transformation of ketones into bromonitroalkanes, this represents a method for the formal synthesis of a-amino acids from ketones.

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Indium-mediated Reformatsky reaction on lactones: preparation of 2-deoxy-2,2′-dimethyl-3-ulosonic acids

Cited by 17 publications

References 30 publications

Natural Products Containing the Oxetane and Related Moieties Present Additional Challenges for Structure Elucidation: A DU8+ Computational Case Study

Natural Products Containing the Oxetane and Related Moieties Present Additional Challenges for Structure Elucidation: A DU8+ Computational Case Study

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Convenient Procedure for the Indium-Mediated Hydroxymethylation of Active Bromo Compounds: Transformation of Ketones into α-Hydroxymethyl Nitroalkanes

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