Selective Monoesterification of Malonic Acid Catalyzed by Boric Acid

Levonis, Stephan M; Bornaghi, Laurent; Houston, Todd Ashley

doi:10.1071/ch07231

Cited by 28 publications

(22 citation statements)

References 16 publications

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“…Craig Hutton reviews the use of boron-based reagents and building blocks in the synthesis of amino acids and peptides, [59] while Todd Houston and coworkers highlight the use of boric and boronic acids to bind and catalyze various transformations of α-hydroxy acids. [60] Dennis Hall [61] and Peter Duggan [62] report new approaches for designing receptors to recognize biologically important oligosaccharides, while new aspects of carborane chemistry, boric acid catalysis, and asymmetric synthesis with boranes, are reported by Lou Rendina, [63] Todd Houston, [64] and Chandra D. Roy [65] respectively.…”

Section: Expanding Research Frontmentioning

confidence: 99%

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Petasis

2007

Aust. J. Chem.

109

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The present essay offers an overview of the latest developments in the chemistry of organoboron compounds. The unique structural characteristics and the versatile reactivity profile of organoboron compounds continue to expand their roles in several areas of chemistry. A growing number of boron-mediated reactions have become vital tools for synthetic chemistry, particularly in asymmetric synthesis, metal-catalyzed processes, acid catalysis, and multicomponent reactions. As a result, boronic acids and related molecules have now evolved as major players in synthetic and medicinal chemistry. Moreover, their remnant electrophilic reactivity, even under physiological conditions, has allowed their incorporation in a growing number of bioactive molecules, including bortezomib, a clinically approved anticancer agent. Finally, the sensitive and selective binding of boronic acids to diols and carbohydrates has led to the development of a growing number of novel chemosensors for the detection, quantification, and imaging of glucose and other carbohydrates. There is no doubt that the chemistry of organoboron compounds will continue to expand into new discoveries and new applications in several fields of science. Long History -Expanding RolesOrganic compounds containing boron have been known for over a century, and many aspects of their chemical properties and reactivity have been known for quite some time. Since the discovery and development of hydroboration, the resulting organoboranes are among the most widely used reagents and intermediates in organic synthesis including asymmetric reactions. Also, early investigations on the chemistry of boron hydrides and carboranes revealed new classes of compounds with unique structure and reactivity that continue to attract attention. Despite these early discoveries, however, the real potential of some of the more versatile and chemically stable organoboron compounds was not realized until recently.Indeed, the growing list of valuable organoboron compounds in addition to organoboranes [1] now includes organoboronic acids and boronates, [2] and more recently organotrifluoroborates.

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Section: Expanding Research Frontmentioning

confidence: 99%

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Petasis

2007

Aust. J. Chem.

109

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“…Therefore, in the following synthesis of the target products, procedure 1 was adopted as the typical method. The possible reaction mechanism is as follows: First monomalonates were produced by the reaction of cinnamic acid and alcohols catalyzed by boric acid [21], then monomalonates reacted with aldehydes, leading to Knoevenagel condensation products catalyzed by piperidine. Finally, the condensed products were decarboxylated under the heating condition and the presence of catalysts gave the title compounds.…”

Section: Resultsmentioning

confidence: 99%

“…Monomalonate can usually be prepared by the reaction of alcohols and Meldrum's acid [20]. Monomalonate can also be synthesized by the monoesterification of malonic acid catalyzed by boric acid [21]. Inspired by this method for monomalonate, we successfully developed a general, efficient, and convenient process for the synthesis of phenylpropanoid esters from malonic acid, alcohols, and corresponding benzaldehydes in one-pot in the presence of boric acid and piperidine.…”

Section: Introductionmentioning

confidence: 98%

One-pot preparation of phenylpropanoid esters co-catalyzed by boric acid and piperidine

Wang¹,

Wei²,

Jiang³

et al. 2011

Res Chem Intermed

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Phenylpropanoid esters, especially those with hydroxyl and/or methoxy groups on the benzene ring, are important medicinal chemicals or intermediates. They are usually prepared by esterification of their corresponding substituted cinnamic acids with various alcohols. However, the esterification procedures often suffer from environmentally hazardous problems when sulfuric acid is used as a catalyst or suffer from unsatisfactory yields and expensive raw material when enzyme is applied as a catalyst. In this paper, a convenient one-pot process for preparing various phenylpropanoid esters from substituted benzaldehydes bearing hydroxyl and/or methoxyl groups has been developed. The alcohols react first with malonic acid catalyzed by boric acid to form monomalonate, then without separation, let the resultant mixture immediately react with the injected various substituted benzaldehydes in the presence of piperidine to afford the desired esters with moderate to good yields.

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“…We required a core salicylate scaffold that could be readily transformed into a variety of derivatives. Here, we describe the synthesis and X-ray crystal structure of 2′propynyl 2-hydroxybenzoate (propargyl salicylate) (I) using our chemoselective method of boric acid-mediated esterification (Houston et al, 2004;2007). Borate can activate hydroxycarboxylic acids such as salicylate toward esterification under mild conditions that are tolerant to acid-labile functional groups such as alkynes.…”

Section: S1 Commentmentioning

confidence: 99%

2-Propynyl 2-hydroxybenzoate

et al. 2009

Self Cite

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The title compound, C10H8O3, has been synthesized as part of our investigations into the generation of new antibacterial agents and serves as a building block for the synthesis of compound libraries. The compound crystallizes with two independent molecules in the asymmetric unit. The transoid propynyl ester groups are coplanar with the 2-hydroxybenzoate group with maximum deviations of −0.3507 (3) and 0.1591 (3) Å for the terminal carbons, with intramolecular O—H⋯O hydrogen bonding providing rigidity to the structure and ensuring that the reactivity of the alkyne is not compromised by steric factors. The propynyl group forms intermolecular C—H⋯O interactions with the phenolic O atom. Supramolecular chains along the b axis are found for both molecules with links by weak O—H⋯O intermolecular interactions in the first independent molecule and C—H⋯O interactions in the second.

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Selective Monoesterification of Malonic Acid Catalyzed by Boric Acid

Cited by 28 publications

References 16 publications

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

One-pot preparation of phenylpropanoid esters co-catalyzed by boric acid and piperidine

2-Propynyl 2-hydroxybenzoate

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