DIASTEREOSELECTIVE ALKYLATION OF CHIRAL DERIVATIVES OF ACETOACETIC ACID

被引:13
作者
MORENOMANAS, M [1 ]
SEBASTIAN, RM [1 ]
VALLRIBERA, A [1 ]
MOLINS, E [1 ]
机构
[1] CSIC,INST CIENCIA MAT,E-08193 CERDANYOLA,SPAIN
关键词
D O I
10.1016/0040-4020(95)00643-M
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-acetoacetyl-(S)-4-benzyloxazolidin-2-one and N-acetoacetyl-(R)-bornane-10,2-sultam are alkylated at the C-alpha of the acetoacetyl moiety with significant diastereoisomeric excesses. The diastereoisomers are in general easily separable and configurationally fairly stable.
引用
收藏
页码:10795 / 10800
页数:6
相关论文
共 7 条
[1]   ASYMMETRIC-SYNTHESIS OF PREMONENSIN, A POTENTIAL INTERMEDIATE IN THE BIOSYNTHESIS OF MONENSIN [J].
EVANS, DA ;
DIMARE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2476-2478
[2]   ASYMMETRIC ACYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - THE 1ST DIRECT APPROACH TO THE CONSTRUCTION OF CHIRAL BETA-DICARBONYL SYNTHONS [J].
EVANS, DA ;
ENNIS, MD ;
LE, T ;
MANDEL, N ;
MANDEL, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1154-1156
[3]   PREPARATION OF TRANSITION-METAL COMPLEXES OF CHIRAL DERIVATIVES OF ACETOACETIC ACID - TETRAALKYLAMMONIUM TETRACHLOROMETALLATES AS AN ORGANIC SOURCE OF METALS [J].
GALVEZ, N ;
MORENOMANAS, M ;
PADROS, I ;
SEBASTIAN, RM ;
SERRA, N ;
VALLRIBERA, A .
POLYHEDRON, 1995, 14 (10) :1397-1399
[4]   ASYMMETRIC DIALKYLATION OF ALPHA-CYANOACETIC ACID [J].
HANAMOTO, T ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1986, 27 (22) :2463-2464
[5]   ASYMMETRIC ACYLATION OF CARBOXAMIDES HAVING TRANS-2,5-BIS (METHOXYMETHOXYMETHYL)PYRROLIDINE MOIETY AS A CHIRAL AUXILIARY AND STEREOSELECTIVE REDUCTION OF THE RESULTING 2-ALKYL-3-OXO AMIDES [J].
ITO, Y ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1984, 25 (52) :6015-6016
[6]   TOTAL SYNTHESIS OF (+)-PEDERIN .2. STEREOCONTROLLED SYNTHESIS OF (+)-BENZOYLSELENOPEDERIC ACID AND TOTAL SYNTHESIS OF (+)-PEDERIN [J].
NAKATA, T ;
NAGAO, S ;
OISHI, T .
TETRAHEDRON LETTERS, 1985, 26 (52) :6465-6468
[7]  
OPPOLZER W, 1987, TETRAHEDRON, V43, P1969, DOI 10.1016/S0040-4020(01)86780-6