ASYMMETRIC CIS-DIHYDROXYLATION OF OLEFINS BY UTILIZING CHIRAL BISPIPERAZINE

被引:32
作者
FUJI, K
TANAKA, K
MIYAMOTO, H
机构
[1] Institute for Chemical Research, Kyoto University, Uji, Kyoto
关键词
ASYMMETRIC OXIDATION; OSMIUM TETROXIDE; PIPERAZINE; CHIRAL LIGAND; CIS-DIHYDROXYLATION;
D O I
10.1016/0040-4039(92)88090-R
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric dihydroxylation of a variety of olefins has been achieved by employing the chiral ligands of N,N'-dialkyl bispiperazines having linker arm of two carbons in excellent to good enantioselectivity.
引用
收藏
页码:4021 / 4024
页数:4
相关论文
共 16 条
[1]   ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].
CHA, JK ;
CHRIST, WJ ;
KISHI, Y .
TETRAHEDRON, 1984, 40 (12) :2247-2255
[2]   ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].
COREY, EJ ;
JARDINE, PD ;
VIRGIL, S ;
YUEN, PW ;
CONNELL, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244
[3]   THE ORIGIN OF ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS BY OSMIUM-TETROXIDE AND CINCHONA ALKALOID DERIVATIVES [J].
COREY, EJ ;
LOTTO, GI .
TETRAHEDRON LETTERS, 1990, 31 (19) :2665-2668
[4]  
Criegee R, 1936, LIEBIGS ANN CHEM, V522, P75
[5]  
HENTGES SG, 1980, J AM CHEM SOC, V102, P4263, DOI 10.1021/ja00532a050
[6]   ASYMMETRIC DIHYDROXYLATION OF ALKENES WITH OSMIUM-TETROXIDE - CHIRAL N,N'-DIALKYL-2,2'-BIPYRROLIDINE COMPLEX [J].
HIRAMA, M ;
OISHI, T ;
ITO, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (10) :665-666
[7]   ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].
JACOBSEN, EN ;
MARKO, I ;
MUNGALL, WS ;
SCHRODER, G ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970
[8]  
JORGENSEN KA, 1990, TETRAHEDRON LETT, V31, P6417
[9]   OSMIUM TETRAOXIDE CATALYZED VICINAL HYDROXYLATION OF HIGHER OLEFINS BY USING HEXACYANOFERRATE(III) ION AS A COOXIDANT [J].
MINATO, M ;
YAMAMOTO, K ;
TSUJI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :766-768
[10]   ASYMMETRIC-SYNTHESIS USING CHIRAL PIPERAZINES .3. ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ARYL ALDEHYDES CATALYZED BY CHIRAL PIPERAZINES [J].
NIWA, S ;
SOAI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2717-2720