Diastereoselective Palladium-Catalyzed α-Arylation of 4-Substituted Cyclohexyl Esters

被引：30

作者：

Bercot, Eric A. ^{[1
]}

Caille, Seb ^{[1
]}

Bostick, Tracy M. ^{[1
]}

Ranganathan, Krishnakumar ^{[1
]}

Jensen, Randy ^{[1
]}

Faul, Margaret M. ^{[1
]}

机构：

[1] Amgen Inc, Chem Proc R&D, Thousand Oaks, CA 91320 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

关键词：

D O I：

10.1021/ol8021758

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective palladium-catalyzed arylation of 4-substituted cyclohexyl esters has been developed. The reaction proceeds at room temperature in the presence of [(t-Bu(3)P)PdBr](2) providing products in up to 37:1 dr.

引用

页码：5251 / 5254

页数：4

共 44 条

[11] Stereoselective formation of quaternary carbon centers and related functions [J].

Denissova, I ;

Barriault, L .

TETRAHEDRON, 2003, 59 (51) :10105-10146

[12] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].

Douglas, CJ ;

Overman, LE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367

[13] Recent developments in the transfer of chirality within enolate alkylation reactions [J].

Eames, J ;

Suggate, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :186-189

[14]

Eliel E.L., 1994, STEREOCHEMISTRY ORGA, P686

[15] Diastereoselectivity in the formation of quaternary centers with aryllead(IV) tricarboxylates [J].

Elliott, GI ;

Konopelski, JP ;

Olmstead, MM .

ORGANIC LETTERS, 1999, 1 (11) :1867-1870

[16] Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions [J].

Groaning, MD ;

Meyers, AI .

TETRAHEDRON, 2000, 56 (51) :9843-9873

[17] Palladium-catalyzed α-arylation of esters and amides under more neutral conditions [J].

Hama, T ;

Liu, XX ;

Culkin, DA ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11176-11177

[18] Palladium-catalyzed α-arylation of esters with chloroarenes [J].

Hama, Takuo ;

Hartwig, John F. .

ORGANIC LETTERS, 2008, 10 (08) :1549-1552

[19] α-arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)3]PdBr}2 [J].

Hama, Takuo ;

Hartwig, John F. .

ORGANIC LETTERS, 2008, 10 (08) :1545-1548

[20] Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383

← 1 2 3 4 5 →