A NEW MODEL FOR THE STEREOSELECTIVITIES OF DIHYDROXYLATIONS OF ALKENES BY CHIRAL DIAMINE COMPLEXES OF OSMIUM TETRAOXIDE

被引：116

作者：

WU, YD ^{[1
]}

WANG, Y ^{[1
]}

HOUK, KN ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 05期

关键词：

D O I：

10.1021/jo00031a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A symmetrical five-membered transition structure model for the dihydroxylations of alkenes by chiral diamine complexes of osmium tetraoxide has been developed based on X-ray crystal structures of OsO4-amine complexes and osmate esters and ab initio transition structures of analogous reactions. The MM2 calculations based upon this model reproduce the stereoselectivities observed with a variety of chiral diamine ligands. Some predictions are also made using this force field.

引用

页码：1362 / 1369

页数：8

共 50 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2] BENZENE, AROMATIC RINGS, VANDERWAALS MOLECULES, AND CRYSTALS OF AROMATIC-MOLECULES IN MOLECULAR MECHANICS (MM3) [J].

ALLINGER, NL ;

LII, JH .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (08) :1146-1153

[3] HIGHLY STEREOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE MASKED SYN-ALPHA-BETA-DIHYDROXY ALDEHYDES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L ;

STEFANELLI, S .

TETRAHEDRON LETTERS, 1987, 28 (27) :3139-3142

[4] MM2 MODEL FOR THE INTRAMOLECULAR ADDITIONS OF ACYL-SUBSTITUTED RADICALS TO ALKENES [J].

BROEKER, JL ;

HOUK, KN .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3651-3655

[5]

Brown F., UNPUB

[6]

BURKERT U, 1980, 406 AM CHEM SOC QUAN

[7] 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

[8] 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

[9] ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED ALKENES BY DIOXIRANE INTERMEDIATES GENERATED FROM POTASSIUM PEROXOMONOSULPHATE AND CHIRAL KETONES [J].

CURCI, R ;

FIORENTINO, M ;

SERIO, MR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) :155-156

[10] ON THE ORIGIN OF PROXIMITY EFFECTS ON REACTIVITY - A MODIFIED MM2 MODEL FOR THE RATES OF ACID-CATALYZED LACTONIZATIONS OF HYDROXY-ACIDS [J].

DORIGO, AE ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (12) :3698-3708

← 1 2 3 4 5 →