ChemInform Abstract: AMINO ACIDS AND PEPTIDES. XXIX. A NEW EFFICIENT ASYMMETRIC SYNTHESIS OF α-AMINO ACID DERIVATIVES WITH RECYCLING OF A CHIRAL REAGENT - ASYMMETRIC ALKYLATION OF A CHIRAL SCHIFF BASE FROM GLYCINE

1978 ◽  
Vol 9 (30) ◽  
Author(s):  
T. OGURI ◽  
N. KAWAI ◽  
T. SHIOIRI ◽  
S. YAMADA
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Asymmetric Alkylation ◽  
Chiral Reagent ◽  
Chiral Schiff Base

Direct asymmetric synthesis of α-deuterated α-amino acid derivatives from the parent α-amino acids via memory of chirality

2018 ◽  
Vol 59 (13) ◽  
pp. 1188-1191 ◽  
Author(s):  
Haruka Ohtsuki ◽  
Megumi Takashima ◽  
Takumi Furuta ◽  
Takeo Kawabata
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Memory Of Chirality

scholarly journals Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

2011 ◽  
Vol 7 ◽  
pp. 1570-1576 ◽  
Author(s):  
Elizabeth P Jones ◽  
Peter Jones ◽  
Andrew J P White ◽  
Anthony G M Barrett
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Coupling Reaction ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Aryl Group ◽  
Hydrolysis Of

A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

scholarly journals Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement

2020 ◽  
Vol 11 (40) ◽  
pp. 10984-10990 ◽  
Author(s):  
Xi-Shang Sun ◽  
Xing-Heng Wang ◽  
Hai-Yan Tao ◽  
Liang Wei ◽  
Chun-Jiang Wang
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Cope Rearrangement ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
High Yields

In this study, we developed an efficient Ir-catalyzed cascade umpolung allylation/2-aza-Cope rearrangement for the preparation of a variety of quaternary trifluoromethyl α-ε-amino acids in high yields with excellent enantioselectivities.

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