Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA

Gaspa, Silvia; Porcheddu, Andrea; Luca, Lidia De

doi:10.1021/acs.orglett.5b01579

Cited by 64 publications

(23 citation statements)

References 66 publications

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“…Dess‐Martin periodinane oxidation led to the aldehyde 35 in 92 % yield. Oxidation and esterification with trichloroisocyanuric acid, NEt 3 and MeOH following a procedure by De Luca et al . did not lead to the methyl ester but a dichlorination of the aromatic ring of chromane 35 .…”

Section: Resultsmentioning

confidence: 99%

Scope and Limitations of the Domino Vinylogous Aldol/oxa‐Michael Reaction

2017

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The asymmetric, atom economic reaction of salicylaldehydes with α,β‐unsaturated aldehydes in the presence of an organocatalyst leads to chiral tricyclic chromanes. In this report, the first exploration of heteroatom‐substituted α,β‐unsaturated aldehydes is demonstrated: We present the investigation of the enantioselective domino vinylogous aldol/oxa‐Michael reaction in respect to its scope and limitations. The chiral chromanes arriving from this reaction are highly functionalized and are versatile synthetic intermediates that can further be converted into the respective tetrahydroxanthones with functionalities on the C‐4a position. A new synthetic route to a methyl ester on this position is developed starting with a p‐methoxyphenyl protected alcohol.

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Section: Resultsmentioning

confidence: 99%

Scope and Limitations of the Domino Vinylogous Aldol/oxa‐Michael Reaction

2017

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“…Indeed, applying Corey–Ganem oxidation conditions (NaCN, AcOH, MeOH) [10] or NHC-catalyzed oxidations [11] provided little or no desired product. Less common conditions such as I 2 /MeOH, TCCA/MeOH, [12] oxone/MeOH, [13] and vanadium catalysis [14] proved unsuccessful as well. A sequential approach to this oxidation through an intermediate carboxylic acid using the Lindgren–Kraus–Pinnick oxidation was equally untenable.…”

Section: Resultsmentioning

confidence: 99%

A sequential cycloaddition strategy for the synthesis of Alsmaphorazine B traces a path through a family of Alstonia alkaloids

Hong

Vanderwal

2017

Tetrahedron

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Driven by a new biogenetic hypothesis, the first total synthesis of alsmaphorazine B and several related indole alkaloids has been achieved. Numerous early approaches proved unsuccessful owing to unproductive side reactivity; nevertheless, they provided important clues that guided the evolution of our strategy. Critical to our success was a major improvement in our Zincke aldehyde cycloaddition strategy, which permitted the efficient gram-scale synthesis of akuammicine. The sequential chemoselective oxidations of akuammicine leading up to the key oxidative rearrangement also yielded several biogenetically related indole alkaloids en route to alsmaphorazine B.

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“…4,5 Benzothiazole derivatives are precious heterocyclic scaffolds present in numerous natural products or synthetic chemicals, offering valuable biological activities. 6,7 Organic structures containing both phenol ester and benzothiazole moieties would benet from both functional parts in terms of pharmaceutical and biological activities.…”

Section: -3mentioning

confidence: 99%

Superparamagnetic nanoparticles as a recyclable catalyst: a new access to phenol esters via cross dehydrogenative coupling reactions

Nguyen

Dang

et al. 2017

RSC Adv.

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CuFe 2 O 4 superparamagnetic nanoparticles were utilized as a recyclable heterogeneous catalyst for the direct synthesis of chemical structures containing both phenol ester and benzothiazole moieties via cross dehydrogenative coupling reactions. Several substrates were reactive towards the transformation in the presence of the nano catalyst, including benzaldehyde, benzyl alcohol, dibenzyl ether, 2-oxo-2-phenylacetaldehyde, and 2-iodo-1-phenylethanone. This nano catalyst displayed higher catalytic efficiency than many homogeneous and heterogeneous catalysts. The nano CuFe 2 O 4 was easily isolated by using a magnet, and reutilize numerous times without a remarkable deterioration in catalytic performance. To our best knowledge, these reactions were not previously reported in the literature.

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Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA

Cited by 64 publications

References 66 publications

Scope and Limitations of the Domino Vinylogous Aldol/oxa‐Michael Reaction

Scope and Limitations of the Domino Vinylogous Aldol/oxa‐Michael Reaction

A sequential cycloaddition strategy for the synthesis of Alsmaphorazine B traces a path through a family of Alstonia alkaloids

Superparamagnetic nanoparticles as a recyclable catalyst: a new access to phenol esters via cross dehydrogenative coupling reactions

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