Multicomponent Reactions with Organoboron Compounds

Petasis, Nicos A.

doi:10.1002/3527605118.ch7

Cited by 34 publications

(20 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on this concept, some time ago we introduced the use of organoboron compounds as key components in multicomponent reactions of amines and carbonyl compounds. [31][32][33][34] Several variations of this type of reaction were introduced, including the synthesis of amino acids, [31] amino alcohols, [32] and amino phenols. [33] Moreover, we and others have shown that this type of process can be used for the synthesis of a large variety of novel amine derivatives, amino sugars, and heterocycles.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

“…[33] Moreover, we and others have shown that this type of process can be used for the synthesis of a large variety of novel amine derivatives, amino sugars, and heterocycles. [34] A notable feature of this chemistry is that it proceeds under mild conditions and can generate directly many types of novel drug-like molecules, making it especially useful for diversity-oriented synthesis [35] and applications in medicinal chemistry. Multicomponent reactions, especially those involving isocyanides, [36] have a long history and have attracted a renewed interest in recent times as a result of new developments in combinatorial chemistry and parallel synthesis.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

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

Petasis

2007

Aust. J. Chem.

Self Cite

109

View full text Add to dashboard Cite

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.

show abstract

Section: Multicomponent Reactionsmentioning

confidence: 99%

Section: Multicomponent Reactionsmentioning

confidence: 99%

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

Petasis

2007

Aust. J. Chem.

Self Cite

109

View full text Add to dashboard Cite

show abstract

“…Petasis reaction of three-component, onepot synthesis has been received intense attention in medicinal and combinatorial chemistry. [1][2][3][4][5][6][7][8][9][10][11] Petasis synthesis can providearylglycines, non-proteinogenic aminoacids. It offers many attractive features to the medicinal chemistry including facile entries to a large number of -arylglycines of new and diverse structures with high atom and step economy.…”

Section: Introductionmentioning

confidence: 99%

Petasis three-component reaction accelerated by trifluoroacetic acid: synthesis of indoline-derived glycines

Zhang

Fan

Xie

et al. 2016

Tetrahedron Letters

View full text Add to dashboard Cite

We have discovered that trifluoroacetic acid is an efficient catalyst to accelerate the Petasis three-component, one-pot process, reducing reaction times, and offering good to excellent yields. A series of azaarene-derived glycines have been successfully achieved via the TFAaccelerated Petasis reaction. To our best knowledge, the use of TFA to accelerate Petasis reaction has not been reported in the literature. By virtue of the operational simplicity, the present TFA-catalyzed Petasis reaction, capable of shortening reaction times, might find applications in other instances of the widely used Petasis reaction.

show abstract

“…[14] Schreiber has shown that the Petasis reaction can be nicely exploited to synthesize a multifunctional template that is suitable for further elaboration by a number of pathways (Scheme 4). [15] For example, coupling of lactol 25, amine 26, and boronic acid 27 gave 28 in good yield.…”

Section: Applications Of the Petasis 3crmentioning

confidence: 99%

Applications of Multicomponent Reactions for the Synthesis of Diverse Heterocyclic Scaffolds

2007

View full text Add to dashboard Cite

The sequencing of multicomponent reactions (MCRs) and subsequent cyclization reactions is a powerful stratagem for the rapid synthesis of diverse heterocyclic scaffolds. The optimal MCR is sufficiently flexible that it can be employed to generate adducts bearing a variety of functional groups that may then be selectively paired to enable different cyclization manifolds, thereby leading to a diverse collection of products. The growing interest in diversity-oriented synthesis has led to increased attention to this paradigm for library synthesis, which has inspired many advances in the design and implementation of MCRs for the construction of diverse heterocyclic scaffolds.

show abstract

Multicomponent Reactions with Organoboron Compounds

Cited by 34 publications

References 51 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

Petasis three-component reaction accelerated by trifluoroacetic acid: synthesis of indoline-derived glycines

Applications of Multicomponent Reactions for the Synthesis of Diverse Heterocyclic Scaffolds

Contact Info

Product

Resources

About