Combinatorial Design of Simplified High-Performance Chiral Phase-Transfer Catalysts for Practical Asymmetric Synthesis of α-Alkyl- and α,α-Dialkyl-α-Amino Acids

2008 ◽  
Vol 3 (8-9) ◽  
pp. 1702-1714 ◽  
Author(s):  
Masanori Kitamura ◽  
Seiji Shirakawa ◽  
Yuichiro Arimura ◽  
Xisheng Wang ◽  
Keiji Maruoka
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
High Performance ◽  
Phase Transfer ◽  
Combinatorial Design ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Chiral Phase Transfer Catalysts

Designer chiral phase-transfer catalysts for green sustainable chemistry

2012 ◽  
Vol 84 (7) ◽  
pp. 1575-1585 ◽  
Author(s):  
Keiji Maruoka
Keyword(s):  
High Performance ◽  
Phase Transfer ◽  
Combinatorial Design ◽  
Ammonium Salts ◽  
Transfer Reactions ◽  
Sustainable Chemistry ◽  
Chiral Phase ◽  
Phase Transfer Catalysts ◽  
Chiral Phase Transfer Catalysts ◽  
Neutral Conditions

A series of chiral quaternary ammonium salts derived from commercially available (R)- or (S)-binaphthol have been designed as new C2-symmetric chiral phase-transfer catalysts. In order to realize the flexible design of these phase-transfer catalysts, the combinatorial design approach has been developed. Chiral high-performance organocatalysts, thus obtained, have been successfully applied to the highly practical asymmetric synthesis of various amino acid derivatives, including α-alkyl and α,α-dialkyl-α-amino acids in addition to alkaloids. Furthermore, several chiral bifunctional phase-transfer catalysts have been designed and synthesized for effecting base-free phase-transfer reactions under essentially neutral conditions in order to realize green sustainable chemistry.

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