ENANTIOMERICALLY PURE EPOXYCHROMANS VIA ASYMMETRIC CATALYSIS

被引:170
作者
LEE, NH [1 ]
MUCI, AR [1 ]
JACOBSEN, EN [1 ]
机构
[1] UNIV ILLINOIS,ROGER ADAMS LAB,DEPT CHEM,URBANA,IL 61801
关键词
D O I
10.1016/S0040-4039(00)93426-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and highly effective process for the asymmetric epoxidation of several 2,2-dimethylchromene derivatives is reported. Catalysis by Mn(salen) complex 4 in all cases affords epoxychromans with > 90% ee, and this method has been applied to the synthesis of two recently developed antihypertensive agents in enantiomerically pure form.
引用
收藏
页码:5055 / 5058
页数:4
相关论文
共 16 条
[1]   REACTION OF SOME CHROMENS AND NAPHTHOPYRANS WITH BROMINE AND CHLORINE .V. PREPARATION OF 6,6-DISUBSTITUTED 4,5-DIHYDRONAPHTHO-(2',1' - 2,3)PYRAN-5-ONES [J].
ABBOTT, JB ;
FRANCE, CJ ;
LIVINGST.R ;
MORREY, DP .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (16) :1472-&
[2]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 4-(CYCLIC AMIDO)-2H-1-BENZOPYRANS [J].
ASHWOOD, VA ;
BUCKINGHAM, RE ;
CASSIDY, F ;
EVANS, JM ;
FARUK, EA ;
HAMILTON, TC ;
NASH, DJ ;
STEMP, G ;
WILLCOCKS, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2194-2201
[3]   4-HETEROCYCLYLOXY-2H-1-BENZOPYRAN POTASSIUM CHANNEL ACTIVATORS [J].
BERGMANN, R ;
EIERMANN, V ;
GERICKE, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2759-2767
[4]   USE OF DIMETHYLDIOXIRANE IN THE PREPARATION OF HIGHLY REACTIVE COMPOUNDS - 1ST DIRECT EPOXIDATION OF PRECOCENES [J].
BUJONS, J ;
CAMPS, F ;
MESSEGUER, A .
TETRAHEDRON LETTERS, 1990, 31 (36) :5235-5236
[5]  
CHANG W, 1991, J ORG CHEM, V56, P2296
[6]  
ELLI SGP, 1977, CHROMENES CHROMANONE, pCH2
[7]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF SUBSTITUTED TRANS-4-AMINO-3,4-DIHYDRO-2,2-DIMETHYL-2H-1-BENZOPYRAN-3-OLS [J].
EVANS, JM ;
FAKE, CS ;
HAMILTON, TC ;
POYSER, RH ;
WATTS, EA .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (11) :1582-1589
[8]  
EVANS JM, 1991, CHEM BRIT, P439
[9]  
GANTEN D, 1990, HDB EXPT PHARM, V93, P656
[10]   ENANTIOSELECTIVE EPOXIDATION OF UNFUNCTIONALIZED OLEFINS USING CHIRAL (SALEN)MANGANESE(III) COMPLEXES [J].
IRIE, R ;
NODA, K ;
ITO, Y ;
KATSUKI, T .
TETRAHEDRON LETTERS, 1991, 32 (08) :1055-1058