ChemInform Abstract: Enantioselective Synthesis of Bis-α-Amino Acid Esters via Asymmetric Phase-Transfer Catalysis.

ChemInform ◽  
2010 ◽  
Vol 30 (19) ◽  
pp. no-no
Author(s):  
Barry Lygo ◽  
John Crosby ◽  
Justine A. Peterson
Keyword(s):  
Amino Acid ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Enantioselective Synthesis ◽  
Amino Acid Esters ◽  
Acid Esters

Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis

ACS Catalysis ◽  
2018 ◽  
Vol 8 (7) ◽  
pp. 5708-5713 ◽  
Author(s):  
Eiji Yamamoto ◽  
Kodai Wakafuji ◽  
Yuho Furutachi ◽  
Kaoru Kobayashi ◽  
Takashi Kamachi ◽  
...  
Keyword(s):  
Amino Acid ◽  
Kinetic Resolution ◽  
Phase Transfer ◽  
Base Hydrolysis ◽  
Amino Acid Esters ◽  
Dynamic Kinetic Resolution ◽  
Protected Amino Acid ◽  
Acid Esters

Enantioselective synthesis of amino acid amides via enzymatic ammoniolysis of amino acid esters

1998 ◽  
Vol 5 (1-4) ◽  
pp. 155-157 ◽  
Author(s):  
M.A.P.J. Hacking ◽  
M.A. Wegman ◽  
J. Rops ◽  
F. van Rantwijk ◽  
R.A. Sheldon
Keyword(s):  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Amino Acid Esters ◽  
Acid Esters

Diastereoselectivity in the Synthesis of Unnatural α-Amino Acid Esters by Phase Transfer Catalysis

2004 ◽  
Vol 59 (3) ◽  
pp. 305-309 ◽  
Author(s):  
Francisco Furtado Tavares Lins ◽  
Lázaro Pereira da Cunha ◽  
Yvone Brígido Memória Pouliquen ◽  
Telma Leda Gomes Lemos ◽  
Marcos Carlos de Mattos
Keyword(s):  
Amino Acid ◽  
Michael Reaction ◽  
Phase Transfer ◽  
Progressive Increase ◽  
Amino Acid Esters ◽  
Catalytic Condition ◽  
Michael Acceptors ◽  
Diastereomeric Excess ◽  
Acid Esters ◽  
The Michael Reaction

Two unnatural α-amino acid esters were prepared in good yields via phase transfer catalyzed Michael addition of ethyl N-acetylaminocyanoacetate to chalcone and benzalketone. For both α- enones, a progressive increase in product diastereomeric excess (d.e.) was observed during the course of reaction, even in the absence of quaternary ammonium salt. However, for a fixed reaction time, higher d.e. values were obtained under phase transfer catalytic condition. Analogous reactions were performed using S-aryl thiocinnamates as Michael acceptors, affording a 2-pyrrolidinone in good yield but low d.e. These results were interpreted on the basis of the reversibility of the Michael reaction

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