A NEW HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF 2,5-DISUBSTITUTED-1,3-DIOXOLAN-4-ONES FROM ALPHA-HYDROXYACIDS

被引:19
作者
CHAPEL, N [1 ]
GREINER, A [1 ]
ORTHOLAND, JY [1 ]
机构
[1] RHONE POULENC AGROCHIM,CTR RECH DARGOIRE,BP 9163,F-69263 LYON 09,FRANCE
关键词
D O I
10.1016/0040-4039(91)80352-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of alpha-hydroxyacids with acetals under weak acid catalysis gave the corresponding dioxolanones with a better diastereomeric ratio than the usual strong acid catalyzed synthesis from aldehydes.
引用
收藏
页码:1441 / 1442
页数:2
相关论文
共 11 条
[1]  
FARINES M, 1970, B SOC CHIM FR, P332
[2]  
GRATER G, 1981, TETRAHEDRON LETT, V22, P4221
[3]   CHIRALITY TRANSFER FROM LACTIC-ACID SELECTIVE SYNTHESIS OF 2,2-DISUBSTITUTED-1,3-DIOXOLAN-4-ONES FROM KETONES AND ACETALS [J].
GREINER, A ;
ORTHOLAND, JY .
TETRAHEDRON LETTERS, 1990, 31 (15) :2135-2138
[4]   OPTICALLY-ACTIVE 2-ETHENYL-1,3-DIOXOLANONES AS 3-CARBON SYNTHONS - ALLYLNICKEL DERIVATIVES AS HOMOENOLATE EQUIVALENTS [J].
KRYSAN, DJ ;
MACKENZIE, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6273-6274
[5]   ENANTIOSELECTIVE SYNTHESES OF ALDOLS AND HOMOALLYLIC ALCOHOLS FROM 1,3-DIOXOLAN-4-ONES USING MANDELIC-ACID AS CHIRAL AUXILIARY [J].
MASHRAQUI, SH ;
KELLOGG, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) :2513-2516
[6]   PYRIDINIUM PARA-TOLUENESULFONATE - MILD AND EFFICIENT CATALYST FOR TETRAHYDROPYRANYLATION OF ALCOHOLS [J].
MIYASHITA, M ;
YOSHIKOSHI, A ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3772-3774
[7]   STEREOCHEMISTRY OF 2,5-DIALKYL DERIVATIVES OF 1,3-DIOXOLONE-(4) AND KINETICS OF THEIR NEUTRAL HYDROLYSIS [J].
SALOMAA, P ;
SALLINEN, K .
ACTA CHEMICA SCANDINAVICA, 1965, 19 (05) :1054-&
[8]   PREPARATIVE CHROMATOGRAPHIC RESOLUTION OF SYNTHETICALLY USEFUL CYCLIC ACETALS [J].
SEEBACH, D ;
MULLER, SG ;
GYSEL, U ;
ZIMMERMANN, J .
HELVETICA CHIMICA ACTA, 1988, 71 (05) :1303-1318
[9]   ALPHA-ALKYLATION OF ALPHA-HETEROSUBSTITUTED CARBOXYLIC-ACIDS WITHOUT RACEMIZATION - EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS [J].
SEEBACH, D ;
NAEF, R ;
CALDERARI, G .
TETRAHEDRON, 1984, 40 (08) :1313-1324