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

被引:10
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] ASSOCIATED OCTEL CO LTD,WIRRAL L65 4HF,ENGLAND
关键词
D O I
10.1039/c39920000830
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Addition of methyllithium followed by tertiary haloalkanes to readily available and air-stable (methyl 2-acetamidoacrylate)tricarbonyliron(0) 1, gives protected beta,beta,beta-trialkyl alpha-amino acids which are hydrolysed to give tert-leucine 10 and the new alpha-amino acids 2-amino-3,3-dimethylpentanoic acid 11 and 2-amino-3,3-dimethylhexanoic acid 12.
引用
收藏
页码:830 / 832
页数:3
相关论文
共 26 条
[1]  
ABDERHALDEN E, 1934, Z PHYSIOL CHEM, V228, P187
[2]   CIRCULAR-DICHROISM OF N-THIOBENZOYL-L-A-AMINO-ACIDS .6. ASSESSMENT OF RESOLUTION OF AMINO-ACIDS AS THEIR N-THIOBENZOYL DERIVATIVES [J].
BARRETT, GC ;
COUSINS, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22) :2313-2315
[3]  
BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[4]   NEW SYNTHESES OF ALPHA-AMINO-ACIDS BASED ON N-ACYLIMINO ACETATES [J].
BRETSCHNEIDER, T ;
MILTZ, W ;
MUNSTER, P ;
STEGLICH, W .
TETRAHEDRON, 1988, 44 (17) :5403-5414
[5]   DIELS-ALDER REACTIONS OF METHYL-N-ACYL-ALPHA,BETA-DEHYDROALANINATES WITH CYCLOPENTADIENE [J].
BUENO, MP ;
CATIVIELA, C ;
FINOL, C ;
MAYORAL, JA ;
JAIME, C .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2182-2186
[6]   NUCLEOPHILIC-ADDITION TO TRICARBONYLIRON COMPLEXES OF ALPHA,BETA-UNSATURATED KETONES AND THE PRODUCTION OF 1,4-DIKETONES [J].
DANKS, TN ;
RAKSHIT, D ;
THOMAS, SE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2091-2093
[7]   COMPLEXES OF METHYL ACETAMIDOCINNAMATE AND METHYL ACETAMIDOACRYLATE WITH CARBONYLIRON [J].
DECIAN, A ;
WEISS, R ;
HAUDEGOND, JP ;
CHAUVIN, Y ;
COMMEREUC, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 187 (01) :73-80
[8]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS [J].
EVANS, DA ;
BRITTON, TC ;
DOROW, RL ;
DELLARIA, JF .
TETRAHEDRON, 1988, 44 (17) :5525-5540
[9]   SYNTHESIS, ENZYMIC DEGRADATION, LIPOPHILIC PROPERTIES, AND BIOLOGICAL-ACTIVITY OF [D-ALANINE2, TERT-BUTYLGLYCINE5]ENKEPHALIN AMIDE [J].
FAUCHERE, JL ;
PETERMANN, C .
HELVETICA CHIMICA ACTA, 1980, 63 (04) :824-831
[10]   SYNTHESIS OF ALPHA-AMINO-ACIDS BY REDUCTION OF ALPHA-OXIMINO ESTERS WITH TITANIUM(III) CHLORIDE AND SODIUM-BOROHYDRIDE [J].
HOFFMAN, C ;
TANKE, RS ;
MILLER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3750-3751