Diversity-driven and facile 1,3-dipolar cycloaddition to access dispirooxindole-imidazolidine scaffolds

2017 ◽  
Vol 15 (41) ◽  
pp. 8705-8708 ◽  
Author(s):  
Yu-Lun Qian ◽  
Peng-Ju Xia ◽  
Jun Li ◽  
Qing-Lan Zhao ◽  
Jun-An Xiao ◽  
...  
Keyword(s):  
Amino Acid ◽  
Dipolar Cycloaddition ◽  
Quaternary Carbon ◽  
Carbon Centers

Diversity-driven three-component 1,3-dipolar cycloaddition of isatin, amino acid and isatin-derived ketimine was developed to facilely assemble dispirooxindole-imidazolidine skeletons bearing vicinal quaternary carbon centers.

scholarly journals Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds

2018 ◽  
Author(s):  
Vincent van der Puyl ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Amino Acid ◽  
Tertiary Amine ◽  
Carbonyl Compounds ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Two Component ◽  
Directing Group

We report a regioselective, nickel-catalyzed <i>syn</i>-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with <i>O</i>-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.

scholarly journals Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds

2018 ◽  
Author(s):  
Vincent van der Puyl ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Amino Acid ◽  
Tertiary Amine ◽  
Carbonyl Compounds ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Two Component ◽  
Directing Group

We report a regioselective, nickel-catalyzed <i>syn</i>-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with <i>O</i>-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.

Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α-Substituted Serines

2009 ◽  
Vol 121 (23) ◽  
pp. 4266-4269 ◽  
Author(s):  
Xavier Ariza ◽  
Josep Cornellà ◽  
Mercè Font-Bardia ◽  
Jordi Garcia ◽  
Jordi Ortiz ◽  
...  
Keyword(s):  
Quaternary Carbon ◽  
Carbon Centers ◽  
Stereocontrolled Synthesis
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