A NEW ALPHA-HALOGLYCINE TEMPLATE FOR THE ASYMMETRIC-SYNTHESIS OF AMINO-ACID DERIVATIVES

被引:19
作者
BADRAN, TW
EASTON, CJ
HORN, E
KOCIUBA, K
MAY, BL
SCHLIEBS, DM
TIEKINK, ERT
机构
[1] UNIV ADELAIDE,DEPT CHEM,GPO BOX 498,ADELAIDE,SA 5001,AUSTRALIA
[2] NATL CHEM LAB,DEPT CHEM,DIV CHEM ANAL & STAND,TSUKUBA,IBARAKI 305,JAPAN
关键词
D O I
10.1016/S0957-4166(00)82336-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reaction of (S)-N,N-diacylvalylglycine anhydride with N-bromosuccinimide afforded the corresponding alpha-bromoglycine derivative, which reacted diastereoselectively with allyltributyltin and deuterium over palladium chloride to give the corresponding alpha-allyl- and alpha-deuterio-glycine derivatives, respectively.
引用
收藏
页码:197 / 200
页数:4
相关论文
共 21 条
[11]  
KANMERA T, 1980, INT J PEPT PROT RES, V16, P280
[12]   DYNAMIC NMR MEASUREMENTS OF BOC-AMINO ESTERS WITH APPLICATION OF LANTHANOID SHIFT-REAGENTS [J].
KESSLER, H ;
MOLTER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (12) :1011-1012
[13]   CONFORMATION OF PROTECTED AMINO-ACIDS .5. APPLICATION OF LANTHANIDE SHIFT REAGENTS FOR CONFORMATIONAL STUDIES OF TERT-BUTOXYCARBONYL ALPHA-AMINO-ACID ESTERS - EQUILIBRIUM CHANGES AND KINETICS OF ISOMERIZATION [J].
KESSLER, H ;
MOLTER, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (19) :5969-5973
[14]   SYNTHESIS OF DIASTEREO- AND ENANTIOMERICALLY PURE ALPHA-AMINO-GAMMA-OXO ACID ESTERS BY REACTION OF ACYLIMINOACETATES WITH ENAMINES DERIVED FROM 6-MEMBERED KETONES [J].
KOBER, R ;
PAPADOPOULOS, K ;
MILTZ, W ;
ENDERS, D ;
STEGLICH, W ;
REUTER, H ;
PUFF, H .
TETRAHEDRON, 1985, 41 (09) :1693-1701
[15]   ASYMMETRIC-SYNTHESIS VIA HETEROCYCLIC INTERMEDIATES .29. ASYMMETRIC-SYNTHESIS OF (R)-BETA-(ALKOXYCARBONYL)ASPARTIC DIESTERS (DERIVATIVES OF (R)-ASA) WITH A CHIRAL CATIONIC AMINO-ACID SYNTHON [J].
SCHOLLKOPF, U ;
NEUBAUER, HJ ;
HAUPTREIF, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (12) :1066-1067
[16]   ELECTROPHILIC GLYCINATES - NEW AND VERSATILE TEMPLATES FOR ASYMMETRIC AMINO-ACID SYNTHESIS [J].
SINCLAIR, PJ ;
ZHAI, D ;
REIBENSPIES, J ;
WILLIAMS, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (05) :1103-1104
[17]  
Williams R., 1989, SYNTHESIS OPTICALLY, V7
[18]   ASYMMETRIC-SYNTHESIS OF (R)[2-(H-1)-H-2]GLYCINE AND (S)-[2-(H-1)-H-2]GLYCINE [J].
WILLIAMS, RM ;
ZHAI, D ;
SINCLAIR, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :5021-5022
[19]   ASYMMETRIC-SYNTHESIS OF BETA-CARBOXYASPARTIC ACID [J].
WILLIAMS, RM ;
SINCLAIR, PJ ;
ZHAI, WX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :482-483
[20]   PRACTICAL ASYMMETRIC SYNTHESES OF ALPHA-AMINO-ACIDS THROUGH CARBON CARBON BOND CONSTRUCTIONS ON ELECTROPHILIC GLYCINE TEMPLATES [J].
WILLIAMS, RM ;
SINCLAIR, PJ ;
ZHAI, D ;
CHEN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1547-1557