Concise synthesis of valuable chiral N -Boc- β -benzyl- β -amino acid via construction of chiral N -Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation

2017 ◽  
Vol 28 (2) ◽  
pp. 471-475 ◽  
Author(s):  
Hong-Tao Jiang ◽  
Hao-Ling Gao ◽  
Cheng-Sheng Ge
Keyword(s):  
Amino Acid ◽  
Conjugate Addition ◽  
Cross Metathesis

scholarly journals Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

2017 ◽  
Vol 13 ◽  
pp. 2153-2156 ◽  
Author(s):  
Shital Kumar Chattopadhyay ◽  
Suman Sil ◽  
Jyoti Prasad Mukherjee
Keyword(s):  
Amino Acid ◽  
Histone Deacetylase ◽  
Building Block ◽  
Suberic Acid ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Important Amino Acid ◽  
New Synthesis ◽  
Cyclic Tetrapeptides ◽  
Derivatives Of

A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.

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

Amino Acid Catalyzed Conjugate Addition of Thiol to Dienone

2013 ◽  
Vol 834-836 ◽  
pp. 450-453
Author(s):  
Han Feng Cui ◽  
Yan Lin ◽  
Hao Fan ◽  
Li De Yu ◽  
Ping Nan Wan
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Room Temperature ◽  
Addition Product ◽  
Conjugate Addition ◽  
Acid Catalyzed

Double conjugate addition of thiols with dienones was catalyzed by amino acids at room temperature in methanol, to afford the corresponding addition product in good to excellent yields.

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 Enantioselective Conjugate Addition of Glycine Imines to Activated Alkenes Catalyzed by Amino-Acid-Derived Chiral Phosphonium Salts

2016 ◽  
Vol 2016 (25) ◽  
pp. 4298-4301 ◽  
Author(s):  
Shan Wen ◽  
Xing Li ◽  
Weijun Yao ◽  
Abdul Waheed ◽  
Nisar Ullah ◽  
...  
Keyword(s):  
Amino Acid ◽  
Conjugate Addition ◽  
Phosphonium Salts

Asymmetric Synthesis of Fluorinated Cyclic β-Amino Acid Derivatives through Cross Metathesis

2006 ◽  
Vol 8 (20) ◽  
pp. 4633-4636 ◽  
Author(s):  
Santos Fustero ◽  
María Sánchez-Roselló ◽  
Juan F. Sanz-Cervera ◽  
José Luis Aceña ◽  
Carlos del Pozo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Cross Metathesis

ChemInform Abstract: Enantioselective Conjugate Addition of Oximes to Trisubstituted β-Nitroacrylates: An Organocatalytic Approach to β2,2-Amino Acid Derivatives.

ChemInform ◽  
2011 ◽  
Vol 42 (12) ◽  
pp. no-no
Author(s):  
Fu-Gen Zhang ◽  
Qing-Qing Yang ◽  
Jun Xuan ◽  
Hai-Hua Lu ◽  
Shu-Wen Duan ◽  
...  
Keyword(s):  
Amino Acid ◽  
Conjugate Addition ◽  
Amino Acid Derivatives
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