Synthesis of N,N′-diferrocenylmethyl-(1S,2S)-1,2-diphenylethanediamine and its application as chiral ligand to the asymmetric dihydroxylation of olefins

被引:0
作者
Li, XS [1 ]
Ge, JF
Kong, LC
机构
[1] Zhejiang Normal Univ, Dept Biol & Chem, Jinhua 321004, Peoples R China
[2] Suzhou Univ, Dept Mat & Engn, Suzhou 215006, Peoples R China
关键词
N,N '-diferrocenylmethyl-(lS,2S)-1,2-diphenylethanediamine; asymmetric dihydroxylation; chiral vicinal diol;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N'-Diferrocenylmethyl-(1S,2S)-1,2-diphenylethanediamine was synthesized by two steps from (1S,2S)-1,2-diphenylethanedianiine and ferrocenealdehyde, and has been used as chiral ligand to asymmetric dihydroxylation of olefins. A good enantioselectivity (71%similar to 86% ee) has been achieved.
引用
收藏
页码:1487 / 1489
页数:3
相关论文
共 9 条
[1]   A new ligand class for the asymmetric dihydroxylation of olefins [J].
Becker, H ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451
[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]   IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].
CRISPINO, GA ;
JEONG, KS ;
KOLB, HC ;
WANG, ZM ;
XU, DQ ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786
[4]   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
[5]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[6]   A free ligand for the asymmetric dihydroxylation of olefins utilizing one-phase catalysis and two-phase separation [J].
Kuang, YQ ;
Zhang, SY ;
Jiang, R ;
Wei, LL .
TETRAHEDRON LETTERS, 2002, 43 (20) :3669-3671
[7]   SYNTHESIS OF CHIRAL 2,3-DISUBSTITUTED 1,4-DIAZABICYCLO[2.2.2]OCTANE - NEW LIGAND FOR THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].
OISHI, T ;
HIRAMA, M .
TETRAHEDRON LETTERS, 1992, 33 (05) :639-642
[8]   ENANTIOFACE DIFFERENTIATION IN CIS DIHYDROXYLATION OF C-C DOUBLE-BONDS BY OSMIUM-TETROXIDE WITH USE OF A CHIRAL DIAMINE WITH D2 SYMMETRY [J].
TOMIOKA, K ;
NAKAJIMA, M ;
KOGA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6213-6215
[9]   A SOLID-TO-SOLID ASYMMETRIC DIHYDROXYLATION PROCEDURE FOR KILOGRAM-SCALE PREPARATION OF ENANTIOPURE HYDROBENZOIN [J].
WANG, ZM ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8302-8303