Asymmetric synthesis of quaternary α-amino acid derivatives and their fluorinated analogues
In this work, we describe the asymmetric synthesis of a series of fluorinated and non-fluorinated quaternary α-amino acid derivatives. This methodology involves the diastereoselective addition of chiral 2- p -tolylsulfinyl benzylcarbanions to either imines containing a 2-furyl moiety or trifluoromet...
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| Veröffentlicht in: | Amino acids 2011-08, Vol.41 (3), p.559-573 |
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| container_title | Amino acids |
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| creator | Fustero, Santos Sánchez-Roselló, María Báez, Claribel del Pozo, Carlos García Ruano, José L. Alemán, José Marzo, Leyre Parra, Alejandro |
| description | In this work, we describe the asymmetric synthesis of a series of fluorinated and non-fluorinated quaternary α-amino acid derivatives. This methodology involves the diastereoselective addition of chiral 2-
p
-tolylsulfinyl benzylcarbanions to either imines containing a 2-furyl moiety or trifluoromethyl α-imino esters. Synthetic practicality of this method is demonstrated by short (two-steps) and convenient preparation of 2-(trifluoromethyl)indoline-2-carboxylates. |
| doi_str_mv | 10.1007/s00726-011-0881-7 |
| format | Article |
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p
-tolylsulfinyl benzylcarbanions to either imines containing a 2-furyl moiety or trifluoromethyl α-imino esters. Synthetic practicality of this method is demonstrated by short (two-steps) and convenient preparation of 2-(trifluoromethyl)indoline-2-carboxylates.</description><subject>Amino acids</subject><subject>Amino Acids - chemical synthesis</subject><subject>Amino Acids - chemistry</subject><subject>Analytical Chemistry</subject><subject>Asymmetry</subject><subject>Biochemical Engineering</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Crystallography, X-Ray</subject><subject>Derivatives</subject><subject>Esters</subject><subject>Fluorination</subject><subject>Halogenation</subject><subject>Imines</subject><subject>Imines - chemistry</subject><subject>Life Sciences</subject><subject>Methodology</subject><subject>Molecular Conformation</subject><subject>Neurobiology</subject><subject>Original Article</subject><subject>Proteomics</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><issn>0939-4451</issn><issn>1438-2199</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtOAyEUhonRaK0-gBvDTjcoh2EGZmkab0kTN7ozIcwAlWYuCjNN-li-iM8kTavLbjgJ5_t_yIfQBdAboFTcxnSwglAAQqUEIg7QBHgmCYOyPEQTWmYl4TyHE3Qa45JSYBKKY3TCgDMugU7Q-11ct60dgq9xXHfDh40-4t7hr1EPNnQ6rPHPN9Gt73qsa2-wscGv9OBXNmLdGZwiPmDXjH3wXcqYdKubfjHaeIaOnG6iPd_NKXp7uH-dPZH5y-Pz7G5O6kwUA6kK50AKbm0py9xUlOra0VwIzrVLny5qxwsmMyO4ZJW0TFMwTtYMmGEmr7Iputr2fob-K707qNbH2jaN7mw_RiVTFQCVkMjrvWSyV4pc5HmeUNiidehjDNapz-Db5EMBVRv9aqtfJf1qo1-JlLnc1Y9Va81_4s93AtgWiGnVLWxQy35Mlpu4p_UXcpmRdQ</recordid><startdate>20110801</startdate><enddate>20110801</enddate><creator>Fustero, Santos</creator><creator>Sánchez-Roselló, María</creator><creator>Báez, Claribel</creator><creator>del Pozo, Carlos</creator><creator>García Ruano, José L.</creator><creator>Alemán, José</creator><creator>Marzo, Leyre</creator><creator>Parra, Alejandro</creator><general>Springer Vienna</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20110801</creationdate><title>Asymmetric synthesis of quaternary α-amino acid derivatives and their fluorinated analogues</title><author>Fustero, Santos ; 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p
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| ispartof | Amino acids, 2011-08, Vol.41 (3), p.559-573 |
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| subjects | Amino acids Amino Acids - chemical synthesis Amino Acids - chemistry Analytical Chemistry Asymmetry Biochemical Engineering Biochemistry Biomedical and Life Sciences Crystallography, X-Ray Derivatives Esters Fluorination Halogenation Imines Imines - chemistry Life Sciences Methodology Molecular Conformation Neurobiology Original Article Proteomics Stereoisomerism Synthesis |
| title | Asymmetric synthesis of quaternary α-amino acid derivatives and their fluorinated analogues |
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