Sigmatropic Rearrangement as Tools for Amino Acid and Peptide Modification: Application of the Allylic Sulfur Ylide Rearrangement to the Preparation of Neoglycoconjugates and Other Conjugates.

ChemInform ◽  
2007 ◽  
Vol 38 (12) ◽  
Author(s):  
David Crich ◽  
Yekui Zou ◽  
Franck Brebion
Keyword(s):  
Amino Acid ◽  
Sigmatropic Rearrangement ◽  
Peptide Modification ◽  
Sulfur Ylide

Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

2018 ◽  
Vol 16 (26) ◽  
pp. 4833-4839 ◽  
Author(s):  
Eiji Tayama ◽  
Sho Sotome
Keyword(s):  
Amino Acid ◽  
Sigmatropic Rearrangement ◽  
Amino Acid Esters ◽  
Acid Esters

A base-induced dearomative [2,3] sigmatropic rearrangement followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters.

scholarly journals Tetrazine-Containing Amino Acid for Peptide Modification and Live Cell Labeling

PLoS ONE ◽  
2015 ◽  
Vol 10 (11) ◽  
pp. e0141918 ◽  
Author(s):  
Zhongqiu Ni ◽  
Lanxia Zhou ◽  
Xu Li ◽  
Jing Zhang ◽  
Shouliang Dong
Keyword(s):  
Amino Acid ◽  
Live Cell ◽  
Cell Labeling ◽  
Peptide Modification ◽  
Live Cell Labeling

Highly Stereoselective [2,3]-Sigmatropic Rearrangement of Sulfur Ylide Generated through Cu(I) Carbene and Sulfides

2005 ◽  
Vol 127 (43) ◽  
pp. 15016-15017 ◽  
Author(s):  
Ming Ma ◽  
Lingling Peng ◽  
Changkun Li ◽  
Xiu Zhang ◽  
Jianbo Wang
Keyword(s):  
Sigmatropic Rearrangement ◽  
Sulfur Ylide

scholarly journals Exploring the Scope of Tandem Palladium and Isothiourea Relay Catalysis for the Synthesis of α-Amino Acid Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2463
Author(s):  
Jacqueline Bitai ◽  
Alexandra M. Z. Slawin ◽  
David B. Cordes ◽  
Andrew D. Smith
Keyword(s):  
Amino Acid ◽  
Transition State ◽  
Quaternary Ammonium ◽  
Palladium Catalyst ◽  
Quaternary Ammonium Salts ◽  
Sigmatropic Rearrangement ◽  
Ammonium Salts ◽  
Amino Acid Derivatives ◽  
Substitution Pattern

The scope and limitations of a tandem N-allylation/[2,3]-rearrangement protocol are investigated through the incorporation of a variety of functional groups within an allylic phosphate precursor. This method uses readily accessible N,N-dimethylglycine aryl esters and functionalized allylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequent enantioselective [2,3]-sigmatropic rearrangement, promoted by the chiral isothiourea tetramisole, generates α-amino acid derivatives with two contiguous stereocenters. The incorporation of electron-withdrawing ester and amide groups gave the best results, furnishing the desired products in moderate to good yields (29–70%), with low diastereocontrol (typically 60:40 dr) but high enantioselectivity (up to 90:10 er). These results indicate that substrate–catalyst interactions in the proposed transition state are sensitive to the substitution pattern of the substrates.

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