SYNTHESIS OF OPTICALLY PURE 4-HYDROXYMETHYLOXAZOLIDINONE AS CHIRAL SERINOL SYNTHON FROM GLYCIDOL

被引:17
作者
KATSUMURA, S
KONDO, A
HAN, QJ
机构
关键词
D O I
10.1246/cl.1991.1245
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Optically pure 3-benzyl-4-hydroxymethyl-2-oxazolidinone and 4-benzoyloxymethyl-2-oxazolidinone as chiral serinol synthons were synthesized from optically active glycidol by intramolecular cyclization via 2,3-epoxycarbamates with strict S(N)2 behavior.
引用
收藏
页码:1245 / 1248
页数:4
相关论文
共 22 条
[1]   ENANTIOSELECTIVE SYNTHESIS OF D-ERYTHRO-SPHINGOSINE [J].
BERNET, B ;
VASELLA, A .
TETRAHEDRON LETTERS, 1983, 24 (49) :5491-5494
[2]  
CAMPBELL MM, 1989, TETRAHEDRON LETT, V30, P1193
[3]   AN ENANTIOSPECIFIC SYNTHESIS OF POLYOXAMIC ACID FROM L-ARABINOSE [J].
DUREAULT, A ;
CARREAUX, F ;
DEPEZAY, JC .
TETRAHEDRON LETTERS, 1989, 30 (34) :4527-4530
[4]  
Evans D. A., 1982, ALDRICHIM ACTA, V15, P23
[5]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[6]   GLYCOSYL ALPHA-AMINO-ACIDS VIA STEREOCONTROLLED BUILDUP OF A PENALDIC ACID EQUIVALENT - A NOVEL SYNTHETIC APPROACH TO THE NUCLEOSIDIC COMPONENT OF THE POLYOXINS AND RELATED SUBSTANCES [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3772-3787
[7]   A STEREODIVERGENT SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE FROM L-SERINE [J].
GARNER, P ;
PARK, JM ;
MALECKI, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4395-4398
[8]   THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364
[9]   SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE DERIVATIVES FROM L-SERINE [J].
HEROLD, P .
HELVETICA CHIMICA ACTA, 1988, 71 (02) :354-362
[10]   NEW ENTRY TO SYN-BETA-HYDROXY-ALPHA-AMINO ACIDS [J].
HIRAMA, M ;
HIOKI, H ;
ITO, S .
TETRAHEDRON LETTERS, 1988, 29 (25) :3125-3128