STEREODIVERGENT SYNTHESIS OF CIS EPOXIDES DERIVED FROM ASYMMETRIZED 2-ALKENYL-1,3-PROPANEDIOLS

被引:17
作者
GUANTI, G [1 ]
BANFI, L [1 ]
MERLO, V [1 ]
NARISANO, E [1 ]
THEA, S [1 ]
机构
[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFATICI & AROMATICI,I-16132 GENOA,ITALY
关键词
D O I
10.1016/S0040-4020(01)80220-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cis epoxides of any desired absolute stereochemistry have been obtained in a high enantio- and diastereo-divergent manner via diastereospecific epoxidation of asymmetrized (Z)-2-alkenyl-1,3-propanediols, in turn obtained through a chemoenzymatic route, and a protection-deprotection 'trick' on hydroxy groups.
引用
收藏
页码:9501 / 9516
页数:16
相关论文
共 29 条
[1]  
BANFI L, IN PRESS
[2]  
BESTMANN HJ, 1983, TOP CURR CHEM, V109, P85
[3]   SYNTHESIS OF AMPHOTERICIN-B .2. FRAGMENT C-D OF THE AGLYCONE [J].
BOSCHELLI, D ;
TAKEMASA, T ;
NISHITANI, Y ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1985, 26 (43) :5239-5242
[4]   SYNTHESIS OF KETOFURANOSIDES BY EPOXIDATION-RING CLOSURE OF ENOL ETHERS [J].
BOSCHETTI, A ;
PANZA, L ;
RONCHETTI, F ;
RUSSO, G ;
TOMA, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3353-3357
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]   ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE AS A HIGHLY STEREODIVERGENT CHIRAL BUILDING BLOCK - PREPARATION OF ALL 4 STEREOISOMERS OF PROTECTED 2-HYDROXYMETHYL-1,3-BUTANEDIOL [J].
GUANTI, G ;
BANFI, L ;
NARISANO, E .
TETRAHEDRON LETTERS, 1990, 31 (44) :6421-6424
[7]   STEREOSELECTIVE EPOXIDATION OF ASYMMETRIZED 2-ALKENYL-1,3-PROPANEDIOLS [J].
GUANTI, G ;
BANFI, L ;
NARISANO, E ;
THEA, S .
TETRAHEDRON LETTERS, 1991, 32 (47) :6943-6946
[8]   PROTECTING GROUP CONTROLLED DIASTEREOSELECTIVE ALLYLATION OF ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDES (BHYMA-STAR) [J].
GUANTI, G ;
BANFI, L ;
NARISANO, E .
TETRAHEDRON LETTERS, 1991, 32 (47) :6939-6942
[9]   CHEMOENZYMATIC PREPARATION OF ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE (THYM-STAR) AND OF ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-STAR) AS NEW HIGHLY VERSATILE CHIRAL BUILDING-BLOCKS [J].
GUANTI, G ;
BANFI, L ;
NARISANO, E .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1540-1554
[10]   CONSTRUCTION OF 4 CONSECUTIVE ASYMMETRIC CENTERS .1. ANTI-SELECTIVE AND SYN-SELECTIVE EPOXIDATION OF BETA-METHYL-CIS-HOMOALLYLIC ALCOHOLS [J].
HANAMOTO, T ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1987, 28 (49) :6191-6194