Three-Component Condensation Leading to β-Amino Acid Diamides:  Convergent Assembly of β-Peptide Analogues

Oaksmith, Jennifer M.; Peters, Ulf; Ganem, Bruce

doi:10.1021/ja0450152

Cited by 46 publications

(38 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[236] The diastereoselective Passerini MCR was recently performed with acyl cyanides instead of classical aldehydes, to yield a 1:1 diastereoisomeric mixture of the expected aalkanoyloxy-a-cyanoamides. [237] Different chiral Cu II -bis(oxazolinyl)pyridine complexes have been proposed for the enantioselective version of the Passerini MCR (up to 98 % ee). [238] The diastereoselectivity in the Ugi four-component reaction is highly dependent on the presence of Lewis acids.…”

Section: Addendum (January 26 2005)mentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

View full text Add to dashboard Cite

Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

show abstract

Section: Addendum (January 26 2005)mentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

View full text Add to dashboard Cite

show abstract

“…Thus, this rearrangement has been applied in the synthesis of peptidomimetics: including -secretase inhibitors [127,128], prolyl endopeptidase inhibitor eurystatin A [129], HIV-protease inhibitors [130], and many others [131][132][133][134][135][136][137]. An O-N intramolecular benzoyl migration was effectively used to obtain the paclitaxel side chain, phenylisoserine [138].…”

Section: Other Application Of O-n Intramolecular Acyl Migration Reactionmentioning

confidence: 99%

Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry

Skwarczynski¹,

Kiso

2007

CMC

View full text Add to dashboard Cite

The O-N intramolecular acyl migration, also named as an acyl shift or acyl transfer reaction, is well-known in organic and peptide chemistry as a simple rearrangement which proceeds under very mild aqueous conditions. Despite a long history with this reaction, its application in medicinal chemistry has only lately been proposed. In the last decade, this reaction has been intensively studied and several applications of this rearrangement in medicinal chemistry have appeared. O-N Intramolecular acyl migration has been employed in "no auxiliary, no byproduct" prodrug strategies (prodrugs of paclitaxel and other taxoids, prodrugs of HIV protease inhibitors), for the synthesis of peptides containing difficult sequences via "O-acyl isopeptide method", including Alzheimer's disease related amyloid beta peptide (Abeta) 1-42, and in the design of pH-, photo- or enzyme-triggered click peptides, as a potential powerful tool for identifying the pathological functions of amyloid beta peptides in Alzheimer's disease. This review summarized recent advances in the application of O-N intramolecular acyl migration with special focus on medicinal chemistry.

show abstract

“…Most importantly, the structure of the reaction product can be easily diversified by flexible variation of all the starting materials. Therefore, multicomponent reactions have become one of the most powerful tools for natural product synthesis and drug discovery from diversity‐oriented synthesis strategy . The applications of multicomponent reactions have also been extended to the field of polymer science, including polymer conjugation, post‐modification, and combination with living/controlled polymerization to produce novel materials with various macromolecular architectures and properties …”

Section: Introductionmentioning

confidence: 99%

“…In fact, the results of existing studies show that sequence distribution markedly influences the melting and crystallization temperatures of synthetic polymers, [5] as well as sequence-regulated backbone structures leading to longer retention of mechanical properties and more sustained release behavior of encapsulated guests in biomedical applications as compared with random copolymers from diversity-oriented synthesis strategy. [44][45][46][47][48][49][50][51][52] The applications of multicomponent reactions have also been extended to the field of polymer science, [53][54][55][56] including polymer conjugation, [57][58][59][60] post-modification, [61][62][63] and combination with living/ controlled polymerization [64][65][66][67] to produce novel materials with various macromolecular architectures and properties. [68][69][70][71][72][73][74][75] Recently, some efficient multicomponent reactions have been introduced in the synthesis of sequence-controlled polymers.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Reactions and Multicomponent Cascade Reactions for the Synthesis of Sequence‐Controlled Polymers

Zhang

You

Hong

2018

Macromol. Rapid Commun.

View full text Add to dashboard Cite

Control over the monomer sequence during polymerization has attracted great attention in polymer science, but it remains a serious challenge. Recently, multicomponent reactions have been playing a significant role in the synthesis of sequence-controlled polymers due to their inherent advantage of combining three or more starting materials in time-saving, one-pot operations to afford complex microstructures. In this feature article, the recent representative developments in the synthesis of sequence-controlled polymers by multicomponent reactions are highlighted to give insight on the design of novel sequence-controlled polymers with sufficient molecular diversity and complexity. The main part of this article is divided into three sections according to the different polymerization strategies using multicomponent reactions: direct multicomponent polymerization, multicomponent cascade polymerization, and iterative multicomponent reaction, respectively. It is anticipated that this feature article may provide some guidance for the fabrication of sequence-controlled polymers by multicomponent reactions.

show abstract

Three-Component Condensation Leading to β-Amino Acid Diamides: Convergent Assembly of β-Peptide Analogues

Cited by 46 publications

References 11 publications

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry

Multicomponent Reactions and Multicomponent Cascade Reactions for the Synthesis of Sequence‐Controlled Polymers

Contact Info

Product

Resources

About