A first asymmetric diamination of olefins

被引：56

作者：

Muñiz, K

Nieger, M

机构：

[1] Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

[2] Univ Bonn, Inst Anorgan Chem, D-53121 Bonn, Germany

来源：

SYNLETT | 2003年 / 02期

关键词：

diamines; asymmetric synthesis; imido complexes; osmium; diastereoselectivity;

D O I：

10.1055/s-2003-36799

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric diarnination of olefins employing stable imidoosmium(VIII) complexes is described for the first time. The reaction is based on the use of chiral acrylic esters and related substrates with enantiopure menthol and 8-phenyl menthol as chiral auxiliaries and gives rise to osmaimidazolidines with good to excellent diastereomeric ratios (LIP to 95:5). Removal of the osmium centre and the chiral auxiliary leads to novel enantiopure 1,2,3-trisubstituted compounds.

引用

页码：211 / 214

页数：4

共 29 条

[11] TERT-BUTYLIMIDO COMPLEXES OF OSMIUM-(VIII), OSMIUM-(VII) AND OSMIUM-(VI) - X-RAY CRYSTAL-STRUCTURES OF [(BUTN)2OS(MU-NBUT)2OS(NBUT)(MU-O)]2, [OS(NBUT)2(MU-NBUT)]2 AND [OS(NBUT)2(MU-NBUT)]2[BF4]2
DANOPOULOS, AA
WILKINSON, G
HUSSAINBATES, B
HURSTHOUSE, MB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1991, (02): : 269 - 275
[12] An efficient asymmetric route to 2,3-diaminobutanoic acids
Han, HS
Yoon, J
Janda, KD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) : 2045 - 2048
[13] Bromine-catalyzed aziridination of olefins. A rare example of atom-transfer redox catalysis by a main group element
Jeong, JU
Tao, B
Sagasser, I
Henniges, H
Sharpless, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (27) : 6844 - 6845
[14] Kolb H. C., 1998, TRANSITION METALS OR, V2, P243
[15] CATALYTIC ASYMMETRIC DIHYDROXYLATION
KOLB, HC
VANNIEUWENHZE, MS
SHARPLESS, KB
[J]. CHEMICAL REVIEWS, 1994, 94 (08) : 2483 - 2547
[16] KOLB HC, 1998, TRANSITION METALS OR, V2, P219
[17] Li GG, 2001, ANGEW CHEM INT EDIT, V40, P4277, DOI 10.1002/1521-3773(20011119)40:22<4277::AID-ANIE4277>3.0.CO
[18] 2-I
[19] Lucet D, 1998, ANGEW CHEM INT EDIT, V37, P2581, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO
[20] 2-L

← 1 2 3 →