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.

One-Pot Asymmetric Synthesis of β-Cyanohydroxymethyl α-Amino Acid Derivatives:  Formation of Three Contiguous Stereogenic Centers

2002 ◽  
Vol 4 (25) ◽  
pp. 4519-4522 ◽  
Author(s):  
Shin-ichi Watanabe ◽  
Armando Córdova ◽  
Fujie Tanaka ◽  
Carlos F. Barbas
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Stereogenic Centers

scholarly journals One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3657-3666 ◽  
Author(s):  
Masaaki Omote ◽  
Atsushi Tarui ◽  
Masakazu Ueo ◽  
Marino Morikawa ◽  
Masahiko Tsuta ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Ester ◽  
Peptide Synthesis ◽  
Ring Opening ◽  
Reactive Intermediates ◽  
One Pot ◽  
Open Chain ◽  
Lactam Ring

α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.

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

One-pot synthesis of β-amino acid derivatives from α-amino acids

2006 ◽  
Vol 47 (49) ◽  
pp. 8757-8760 ◽  
Author(s):  
Carlos J. Saavedra ◽  
Rosendo Hernández ◽  
Alicia Boto ◽  
Eleuterio Álvarez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
One Pot Synthesis

One-Pot Synthesis of β-Amino Acid Derivatives from α-Amino Acids.

ChemInform ◽  
2007 ◽  
Vol 38 (13) ◽  
Author(s):  
Carlos J. Saavedra ◽  
Rosendo Hernandez ◽  
Alicia Boto ◽  
Eleuterio Alvarez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
One Pot Synthesis
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