Chloride ion effects on kinetic resolution in Pd-catalysed allylic alkylation

被引：62

作者：

Lloyd-Jones, GC ^{[1
]}

Stephen, SC ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 21期

关键词：

D O I：

10.1039/a806324i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chloride ion (5 mol%) accelerates and stabilises the oxidative addition of the slow-reacting enantiomer of cyclopentenyl pivaloate to Pd-o complexes bearing the Trost modular ligand.

引用

页码：2321 / 2322

页数：2

共 22 条

[1] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS [J].

AMATORE, C ;

JUTAND, A ;

SUAREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9531-9541

[2] A remarkable anion effect on the enantioselectivity of the Pd-catalyzed allylic amination using ferrocenyl ligands [J].

Burckhardt, U ;

Baumann, M ;

Togni, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :155-159

[3] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].

CONSIGLIO, G ;

WAYMOUTH, RM .

CHEMICAL REVIEWS, 1989, 89 (01) :257-276

[4] Chloride effect on the palladium-catalyzed allylic substitution vs elimination of cyclic vinyloxazolidinones and oxazolines [J].

Cook, GR ;

Shanker, PS .

TETRAHEDRON LETTERS, 1998, 39 (28) :4991-4994

[5] TO WHAT EXTENT IS A PI-ALLYLIC INTERMEDIATE INVOLVED IN SOME PALLADIUM-CATALYZED ALKYLATIONS [J].

FIAUD, JC ;

MALLERON, JL .

TETRAHEDRON LETTERS, 1981, 22 (15) :1399-1402

[6] Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides:: Kinetic resolution of the allylic substrate by a chiral Pd-complex [J].

Gais, HJ ;

Eichelmann, H ;

Spalthoff, N ;

Gerhards, F ;

Frank, M ;

Raabe, G .

TETRAHEDRON-ASYMMETRY, 1998, 9 (02) :235-248

[7] STEREOCHEMISTRY OF ALLYLIC REARRANGEMENTS .13. RACEMIZATION, CARBOXYL-OXYGEN EQUILIBRATION AND SOLVOLYSIS OF TRANS-ALPHA,GAMMA-DIMETHYLALLYL P-NITROBENZOATE IN AQUEOUS ACETONE [J].

GOERING, HL ;

MCMICHAEL, KD ;

POMBO, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (07) :965-&

[8] MECHANISM OF APPARENT PI-ALLYL ROTATION IN (PI-ALLYL)PALLADIUM COMPLEXES WITH BIDENTATE NITROGEN LIGANDS [J].

GOGOLL, A ;

ORNEBRO, J ;

GRENNBERG, H ;

BACKVALL, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3631-3632

[9] KINETIC RESOLUTION OF RACEMIC ALLYL ACETATES IN ASYMMETRIC ALLYLIC ALKYLATION CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE PALLADIUM COMPLEX [J].

HAYASHI, T ;

YAMAMOTO, A ;

ITO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (14) :1090-1092

[10] Retention of regiochemistry of allylic esters in palladium-catalyzed allylic alkylation in the presence of a MOP ligand [J].

Hayashi, T ;

Kawatsura, M ;

Uozumi, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1681-1687

← 1 2 3 →