Versatile Access to 2‐Aminocyclobutene‐1‐carboxylic Acid Derivatives and Their Incorporation into Small Peptides

Meijere, Armin de; Limbach, Michael; Janssen, André; Lygin, Alexander V.; Korotkov, Vadim S.

doi:10.1002/ejoc.201000283

Cited by 9 publications

(6 citation statements)

References 42 publications

(13 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally transformations such as reduction of aminocyclobutenes [193] or Curtius rearrangement of cyclobutyl half-esters [194] were employed to access DA aminocyclobutanes. However as they do not imply the construction of the four-membered ring, we will not describe them further in this thesis.…”

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

Nanteuil¹

2016

Springer Theses

View full text Add to dashboard Cite

Section: Synthesismentioning

confidence: 99%

“…Carbamate protected enamine 195 (a, Scheme 2.2) was synthesized by a Curtius rearrangement on acryloyl chloride (193) [2]. Vinyl oxazolidinone 185 (b, Scheme 2.2) was synthesized in one step using a palladium-catalyzed vinyl transfer [3].…”

Section: Discovery Of the Reaction And Optimizationmentioning

confidence: 99%

Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

Nanteuil¹

2016

Springer Theses

View full text Add to dashboard Cite

“…The resulting adduct could be hydrolyzed to afford densely substituted cyclobutanones in a highly regio‐ and stereoselective fashion. Cyclobutenamines have been previously synthesized from the corresponding cyclobutanones or more frequently by [2+2] cycloaddition between an ynamine and a C=C bond [23–30] . However, the ynamine usually carries stabilizing electron withdrawing substituents on the nitrogen and/or at the terminal carbon, which significantly decreases the reactivity of the corresponding enamine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Substituted Cyclobutanones by a One‐Pot Keteniminium‐Enamine Process

Dagoneau

Kolleth

Quinodoz

et al. 2021

Helvetica Chimica Acta

View full text Add to dashboard Cite

Herein, we describe an effective one‐pot sequence for the regio‐ and stereoselective synthesis of highly substituted cyclobutanones. This process relies on first a [2+2] cycloaddition involving a keteniminium salt intermediate with an alkene followed by isomerization of the resulting cyclobutaniminium salt into its cyclic enamine form and then reaction of the latter with an electrophile. The adduct can be either hydrolyzed or reduced to give the corresponding cyclobutanone or cyclobutanamine, respectively, with excellent diastereocontrol. A variety of electrophiles was tolerated allowing the incorporation of diverse substituents and functionalities onto the cyclobutyl ring. Additionally, the coplanarity of diverse cyclic enamines was investigated through a DFT study.

show abstract

“…The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)-and (trans,cis)-beta-dipeptides while the formation of six-membered rings is preferred for the (cis,trans) beta-dipeptide similarly to the previously described (cis,cis)-diastereomer (71). Likewise 2-aminocyclobutene-1-carboxylic acid was prepared (3) and incorporated to some small peptides (40,62) as well as unsaturated derivative, 2-aminocyclobutene-1carbocylic acid (40).…”

Section: Introductionmentioning

confidence: 99%

Β-Amino ACIDS AND THEIR NATURAL BIOLOGICALLY ACTIVE DERIVATIVES. 5. DERIVATIVES OF UNUSUAL ALICYCLIC AND HETEROCYCLIC Β-Amimo ACIDS

Patočka¹

2011

MMSL

View full text Add to dashboard Cite

α-Amino carboxylic acids are one of five major classes of natural products and play a crucial role in diverse biological functions. Historically, the amino acids have been subdivided into proteinogenic and nonproteinogenic respresentatives. β-Amino acids are similar to alfa-amino acids in that they contain an amino terminus and a carboxyl terminus. However, in β-amino acids two carbon atoms separate these functional termini. β-Amino acids, with a specific side chain, can exist as the R or S isomers at either the α(C2) carbon or the β(C3) carbon. This results in a total of 4 possible diastereoisomers for any given side chain. β-Amino acids are not proteinogenic amino acids, but some of them are constituents of soma natural and biologically active compounds.Unusual β-amino acids are alicyclic β-amino acids and heterocyclic β-amino acids. Alicyclic β-amino acids, in which both the β-amino and the acids functionality are vicinally attached to an aliphatic ring, still represent a demanding challenge to the synthetic chemist. One reason for this lies in the intriguing difficulty associated with controlling the absolute and relative stereochemistry of two adjacent stereocenters. In heterocyclic β-amino acids the nitrogen of amino group is a part of nitrogen heterocycles. Some natural derivatives of alicyclic β-amino acids and heterocyclic β-amino acids, their chemical structures and biological activities are discussed in this mini-review.

show abstract

Versatile Access to 2‐Aminocyclobutene‐1‐carboxylic Acid Derivatives and Their Incorporation into Small Peptides

Cited by 9 publications

References 42 publications

Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

Synthesis of Highly Substituted Cyclobutanones by a One‐Pot Keteniminium‐Enamine Process

Β-Amino ACIDS AND THEIR NATURAL BIOLOGICALLY ACTIVE DERIVATIVES. 5. DERIVATIVES OF UNUSUAL ALICYCLIC AND HETEROCYCLIC Β-Amimo ACIDS

Contact Info

Product

Resources

About