REGIOSELECTIVE AND ENANTIOSPECIFIC SYNTHESIS OF 6-SUBSTITUTED AND 5,6-DISUBSTITUTED HEXAHYDROPYRIMIDINES

被引:9
作者
GARRATT, PJ [1 ]
THORN, SN [1 ]
WRIGGLESWORTH, R [1 ]
机构
[1] SANDOZ INST MED RES,LONDON WC1E 6BN,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)74861-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preference for 5- over 6-membered rings in the intramolecular cyclisation of amines with diesters can be partially overcome with mixed methyl (or benzyl), tert-butyl diesters, and this effect is enhanced where there is a beta-substituent. The hexahydropyrimidines are formed enatiospecifically, the amount of racemization usually being less with a beta-substituent present.
引用
收藏
页码:691 / 694
页数:4
相关论文
共 6 条
[1]   NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - SYNTHESIS OF BETA, GAMMA-UNSATURATED ALPHA-AMINO-ACIDS FROM ASPARTIC-ACID [J].
BALDWIN, JE ;
MOLONEY, MG ;
NORTH, M .
TETRAHEDRON, 1989, 45 (19) :6319-6330
[2]   NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS [J].
BALDWIN, JE ;
MOLONEY, MG ;
NORTH, M .
TETRAHEDRON, 1989, 45 (19) :6309-6318
[3]  
BESSE R, 1990, IN PRESS TETRAHEDRON
[4]   POLYPEPTIDES .18. SYNTHESES OF POLY-(BETA-ASPARTIC ACID) AND POLY-(GAMMA GLUTAMIC-ACID) AND THEIR BENZYL ESTERS [J].
HARDY, PM ;
RYDON, HN ;
HAYLOCK, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (04) :605-&
[5]   A WIDELY USEFUL CHIRAL STATIONARY PHASE FOR THE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY SEPARATION OF ENANTIOMERS [J].
PIRKLE, WH ;
FINN, JM ;
SCHREINER, JL ;
HAMPER, BC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3964-3966
[6]  
SCHON I, 1983, INT J PEPT PROT RES, V22, P92