A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers

2016 ◽  
Vol 14 (27) ◽  
pp. 6457-6462 ◽  
Author(s):  
Xiang Li ◽  
Ya Li ◽  
Huaqi Shang
Keyword(s):  
Amino Acids ◽  
Type Reaction ◽  
Carbon Centers ◽  
Fluorinated Carbon

A diastereoselective Mannich-type reaction of α-alkyl, α-aryl, and α-vinyl fluoroacetates with N-tert-butylsulfinyl imines to access highly functionalized β-amino acids has been developed.

Construction of Asymmetric Fluorinated Carbon Centers

2006 ◽  
Vol 45 (14) ◽  
pp. 2172-2174 ◽  
Author(s):  
G. K. Surya Prakash ◽  
Petr Beier
Keyword(s):  
Carbon Centers ◽  
Fluorinated Carbon

scholarly journals Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles

2016 ◽  
Vol 12 ◽  
pp. 2099-2103 ◽  
Author(s):  
Masahiro Torii ◽  
Kohsuke Kato ◽  
Daisuke Uraguchi ◽  
Takashi Ooi
Keyword(s):  
High Fidelity ◽  
Catalytic Method ◽  
Type Reaction ◽  
Carbon Centers ◽  
Axially Chiral

A highly diastereo- and enantioselective Mannich-type reaction of 3-aryloxindoles with N-Boc aldimines was achieved under the catalysis of axially chiral ammonium betaines. This catalytic method provides a new tool for the construction of consecutive quaternary and tertiary stereogenic carbon centers on biologically intriguing molecular frameworks with high fidelity.

scholarly journals Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids

2011 ◽  
Vol 346 (14) ◽  
pp. 2104-2112 ◽  
Author(s):  
Katalin Czifrák ◽  
Viktor Gyóllai ◽  
Katalin E. Kövér ◽  
László Somsák
Keyword(s):  
Amino Acids ◽  
Type Reaction

Catalytic Asymmetric Construction of Halogenated Stereogenic Carbon Centers by Direct Vinylogous Mannich-Type Reaction

2018 ◽  
Vol 140 (45) ◽  
pp. 15170-15175 ◽  
Author(s):  
Feng Zhong ◽  
Wen-Jun Yue ◽  
Hai-Jun Zhang ◽  
Cheng-Yuan Zhang ◽  
Liang Yin
Keyword(s):  
Type Reaction ◽  
Carbon Centers ◽  
Catalytic Asymmetric

scholarly journals Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3405
Author(s):  
Jakub Adamek ◽  
Anna Węgrzyk-Schlieter ◽  
Klaudia Steć ◽  
Krzysztof Walczak ◽  
Karol Erfurt
Keyword(s):  
Amino Acids ◽  
Protecting Group ◽  
Type Reaction ◽  
Wide Range

In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.

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