Highly efficient regio-selective ring-opening nucleophilic fluorination of aziridines and azetidines: access to β- or γ-fluorinated amino acid derivatives

2019 ◽  
Vol 17 (15) ◽  
pp. 3797-3804 ◽  
Author(s):  
Liping Zhu ◽  
Jiale Xiong ◽  
Junkai An ◽  
Nannan Chen ◽  
Jijun Xue ◽  
...  
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Amino Acid Derivatives ◽  
Highly Efficient ◽  
Selective Ring Opening ◽  
Nucleophilic Fluorination

The strategy is mild and efficient, useful in synthesizing β- or γ-fluorinated amines and enantioenriched β-fluoro-α-amino acid derivatives.

Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

Synlett ◽  
2021 ◽  
Author(s):  
Loránd Kiss ◽  
Zsanett Benke ◽  
Melinda Nonn ◽  
Attila M. Remete ◽  
Santos Fustero
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Nitrile Oxide ◽  
Amino Acid Derivatives ◽  
Selective Synthesis ◽  
Chemical Transformations ◽  
Bond Functionalization ◽  
Cross Metathesis ◽  
Chlorosulfonyl Isocyanate ◽  
Biological Potential

AbstractThis Account gives an insight into the selective functionalization of some readily available commercial cyclodienes across simple chemical transformations into functionalized small-molecular scaffolds. The syntheses involved selective cycloadditions, followed by ring-opening metathesis (ROM) of the resulting azetidin-2-one derivatives or isoxazoline frameworks and selective cross metathesis (CM) by discrimination of the C=C bonds on the alkenylated heterocycles. The CM protocols have been described when investigated under various conditions with the purpose on exploring chemodifferentiation of the olefin bonds and a study on the access of the corresponding functionalized β-lactam or isoxazoline derivatives is presented. Due to the expanding importance of organofluorine chemistry in drug research as well as of the high biological potential of β-lactam derivatives several illustrative examples to the access of some fluorine-containing molecular entities is also presented in this synopsis.1 Introduction2 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Chlorosulfonyl Isocyanate Cycloaddition3 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Nitrile Oxide Cycloaddition4 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Metathesis5 Functionalization of sSome Cyclodienes across Nitrile Oxide Cycloaddition6 Selective Synthesis of Functionalized Alicycles across Ring-Opening Metathesis7 Selective Synthesis of Functionalized Alicycles through Cross Metathesis8 Summary and Outlook9 List of Abbreviations

Enantioselective conjugate addition of hydroxylamines to α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal Rh(iii) complex

2017 ◽  
Vol 4 (4) ◽  
pp. 573-577 ◽  
Author(s):  
Tao Deng ◽  
Ganesh Kumar Thota ◽  
Yi Li ◽  
Qiang Kang
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Conjugate Addition ◽  
Amino Acid Derivatives ◽  
Highly Efficient

A highly efficient chiral-at-metal Rh(iii) complex catalyzed asymmetric aza-Michael addition was developed, affordingN-protected β-amino acid derivatives with excellent enantioselectivity.

Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides – towards kinase-like reactivity

2014 ◽  
Vol 50 (88) ◽  
pp. 13608-13611 ◽  
Author(s):  
James I. Murray ◽  
Rudiger Woscholski ◽  
Alan C. Spivey
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Highly Efficient

The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.

scholarly journals Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives

2018 ◽  
Vol 5 (16) ◽  
pp. 2458-2462 ◽  
Author(s):  
Giacomo Berton ◽  
Giuseppe Borsato ◽  
Roberta Zangrando ◽  
Andrea Gambaro ◽  
Fabrizio Fabris ◽  
...  
Keyword(s):  
Ring Opening ◽  
Efficient Synthesis ◽  
Highly Efficient ◽  
Selective Ring Opening

C3-Symmetric tris-benzyl-O-substituted hexahydroxytriphenylene (HHTP) was prepared through selective ring opening with DIBAL-H in 48% yield (38% from HHTP in a two-step synthesis).

Living Ring-Opening Metathesis Polymerization of Enantiopure Norbornene-type β-Amino Acid Derivatives

Synlett ◽  
2001 ◽  
Vol 2001 (12) ◽  
pp. 1875-1877 ◽  
Author(s):  
Carsten Bolm ◽  
Christian L. Dinter ◽  
Ingo Schiffers ◽  
Laurent Defrère
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Amino Acid Derivatives ◽  
Ring Opening Metathesis Polymerization ◽  
Metathesis Polymerization
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