A STUDY OF THE REACTIVITY OF (METHYL 2-ACETAMIDOACRYLATE)-TRICARBONYLIRON(0) LEADING TO A NOVEL SYNTHESIS OF BETA,BETA,BETA-TRIALKYL ALPHA-AMINO-ACIDS

被引：4

作者：

BARKER, J

COOK, SL

LASTERRASANCHEZ, ME

THOMAS, SE

机构：

[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

[2] ASSOC OCTEL CO LTD,WIRRAL L65 4HF,ENGLAND

来源：

INORGANICA CHIMICA ACTA | 1994年 / 220卷 / 1-2期

关键词：

IRON COMPLEXES; CARBONYL COMPLEXES; AMINO ACID COMPLEXES;

D O I：

10.1016/0020-1693(94)03866-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(Methyl 2-acetamidoacrylate)tricarbonyliron(0) (3) reacts with 2 equivalents of methyllithium to give methyl N-acetylalaninate (4) and 2-acetamido-4-oxopentanoate (5) when the reaction is quenched with trifluoroacetic acid. Production of methyl N-acetylalaninate is dependent only on the presence of trifluoroacetic acid, and the ratio of 4 to 5 generated in these reactions is related to the quantity of trifluoroacetic acid used to quench them. Addition of two equivalents of methyllithium followed by tertiary haloalkanes gives protected beta,beta,beta-trialkyl alpha-amino acids which may be hydrolysed to give tert-leucine (13) and the new alpha-amino acids 2-amino-3,3-dimethylpentanoic acid (14) and 2-amino-3,3-dimethylhexanoic acid (15).

引用

页码：137 / 143

页数：7

共 29 条

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[2] SURPRISING REACTIVITY OF (METHYL 2-ACETAMIDOACRYLATE)TRICARBONYLIRON(0) LEADING TO THE SYNTHESIS OF BETA,BETA,BETA-TRIALKYL ALPHA-AMINO-ACIDS [J].