Highly Diastereoselective Reaction of α-Diazoesters with Aryl Alcohols and Isatin Imines: Rapid Access to Oxindole-Derived α-Alkoxy-β-amino Acid Derivatives with Two Adjacent Quaternary Carbon Centers

2014 ◽  
Vol 2014 (11) ◽  
pp. 2221-2224 ◽  
Author(s):  
Tamilselvan Rajasekaran ◽  
Govindaraju Karthik ◽  
B. Sridhar ◽  
S. Kiran Kumar ◽  
Basi V. Subba Reddy
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Rapid Access ◽  
Diastereoselective Reaction

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.

Preparation of Cyclic β-Amino Acid Derivatives with Quaternary Carbon Center via a Radical Addition-Cyclization Sequence

Heterocycles ◽  
2014 ◽  
Vol 89 (1) ◽  
pp. 143 ◽  
Author(s):  
Okiko Miyata ◽  
Norihiko Takeda ◽  
Masafumi Ueda ◽  
Seiko Kajisa ◽  
Kenji Matsuno ◽  
...  
Keyword(s):  
Amino Acid ◽  
Radical Addition ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon

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.

Enantioselective oxidative functionalization of the Csp3–H bond adjacent to a nitrogen atom for rapid access to β-hydroxyl-α-amino acid derivatives

2016 ◽  
Vol 52 (79) ◽  
pp. 11831-11833 ◽  
Author(s):  
Lin Qiu ◽  
Xin Guo ◽  
Yu Qian ◽  
Changcheng Jing ◽  
Chaoqun Ma ◽  
...  
Keyword(s):  
Amino Acid ◽  
Nitrogen Atom ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Oxidative Functionalization ◽  
Mild Conditions ◽  
Rapid Access

Highly chemoselective and enantioselective one-pot reactions involved in the oxidative functionalization of Csp3–H bonds adjacent to nitrogen atoms were developed to rapidly construct highly functionalized β-hydroxyl-α-amino acid derivatives from simple starting materials under mild conditions.

Rapid Access to α-Alkoxy and α-Amino Acid Derivatives through Safe Continuous-Flow Generation of Diazoesters

2011 ◽  
Vol 17 (35) ◽  
pp. 9586-9589 ◽  
Author(s):  
Hannah E. Bartrum ◽  
David C. Blakemore ◽  
Christopher J. Moody ◽  
Christopher J. Hayes
Keyword(s):  
Amino Acid ◽  
Continuous Flow ◽  
Amino Acid Derivatives ◽  
Rapid Access ◽  
Flow Generation

ChemInform Abstract: Preparation of Cyclic β-Amino Acid Derivatives with Quaternary Carbon Center via a Radical Addition-Cyclization Sequence.

ChemInform ◽  
2014 ◽  
Vol 45 (23) ◽  
pp. no-no
Author(s):  
Okiko Miyata ◽  
Norihiko Takeda ◽  
Masafumi Ueda ◽  
Seiko Kajisa ◽  
Kenji Matsuno ◽  
...  
Keyword(s):  
Amino Acid ◽  
Radical Addition ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon
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