Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process

2012 ◽  
Vol 48 (39) ◽  
pp. 4713 ◽  
Author(s):  
Zhi-Cong Geng ◽  
Ning Li ◽  
Jian Chen ◽  
Xiao-Fei Huang ◽  
Bin Wu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Opening Process

Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation

2016 ◽  
Vol 14 (42) ◽  
pp. 10080-10089 ◽  
Author(s):  
Nozomi Saito ◽  
Iman Abdullah ◽  
Kayoko Hayashi ◽  
Katsuyuki Hamada ◽  
Momoko Koyama ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Active Form ◽  
Asymmetric Hydrogenation ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives

Nickel-promoted carboxylation of ynamides followed by rhodium-catalyzed asymmetric hydrogenation provided α-substituted-β-amino acids in an optically active form.

An enantioselective synthesis of β2-amino acid derivatives

2005 ◽  
Vol 16 (7) ◽  
pp. 1309-1319 ◽  
Author(s):  
Jomana Elaridi ◽  
Ali Thaqi ◽  
Andrew Prosser ◽  
W. Roy Jackson ◽  
Andrea J. Robinson
Keyword(s):  
Amino Acid ◽  
Enantioselective Synthesis ◽  
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

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Synthesis of Optically Active 2,3-Disubstituted Indoline ­Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles

Synlett ◽  
2018 ◽  
Vol 29 (04) ◽  
pp. 530-536 ◽  
Author(s):  
Takashi Ikawa ◽  
Shuji Akai ◽  
Yuta Sumii ◽  
Shigeaki Masuda ◽  
Ding Wang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cycloaddition Reaction ◽  
Optically Active ◽  
Amino Acid Derivatives ◽  
Cycloaddition Reactions

We report a method for synthesizing optically active 2,3-disubstituted indolines by the cycloaddition reaction of benzynes with various 4-[(4-toluenesulfonyl)amino]-(E)-but-2-enenitriles, which are readily prepared from the corresponding l-amino acid derivatives.

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