Asymmetric palladium-catalyzed benzylic nucleophilic substitution:: high enantioselectivity with the DUPHOS family ligands

被引：29

作者：

Assié, M ^{[1
]}

Legros, JY ^{[1
]}

Fiaud, JC ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, CNRS, UMR 8075,Lab Catalyse Mol, F-91405 Orsay, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2005.01.032

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric palladium-catalyzed benzylic reaction of 1-(2-naphthyl)ethyl acetate and its 6-methoxy substituted analogue with dimethyl malonate anion led to substitution products with up to 90% ee when the iPr-DUPHOS chiral ligand was used. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1183 / 1187

页数：5

共 20 条

[1] PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 2,3-BUTADIANYLMALONATES TO GAMMA-LACTONES [J].

BESSON, L ;

BAZIN, J ;

GORE, J ;

CAZES, B .

TETRAHEDRON LETTERS, 1994, 35 (18) :2881-2884

[2] Arylmethyl esters as protecting groups for carboxylic, carbonic and carbamic acids: deprotection via homogeneous palladium-catalyzed hydrogenolysis [J].

Boutros, A ;

Legros, JY ;

Fiaud, JC .

TETRAHEDRON LETTERS, 1999, 40 (41) :7329-7332

[3] 4-Quinolylmethyl and 1-naphthylmethyl as benzyl-type protecting groups of carboxylic acids removable by homogeneous palladium-catalyzed hydrogenolysis [J].

Boutros, A ;

Legros, JY ;

Fiaud, JC .

TETRAHEDRON, 2000, 56 (15) :2239-2246

[4] SYNTHESIS OF A REVERSE ESTER ANALOG OF 1,2-SN-DIGLYCERIDES FROM (S)-1,2-DI-O-ISOPROPYLIDENEGLYCEROL - EFFICIENT, STEREOSPECIFIC NUCLEOPHILIC DISPLACEMENT VIA A TRIFLATE AT GLYCEROL C-2 [J].

GOLDING, BT ;

GRIFFIN, AL ;

ROBINSON, DH .

TETRAHEDRON LETTERS, 1993, 34 (40) :6459-6462

[5] Palladium catalysed [2+2+1] intramolecular cycloaddition for the preparation of bicyclo[3.3.0]octa-1.5-dien-3-ones from 1,6-diynes [J].

Grigg, R ;

Zhang, LX ;

Collard, S ;

Keep, A .

CHEMICAL COMMUNICATIONS, 2003, (15) :1902-1903

[6] SYNTHETIC APPLICATIONS OF DEALKOXYCARBONYLATIONS OF MALONATE ESTERS, BETA-KETO-ESTERS, ALPHA-CYANO ESTERS AND RELATED-COMPOUNDS IN DIPOLAR APROTIC MEDIA .2. [J].

KRAPCHO, AP .

SYNTHESIS-STUTTGART, 1982, (11) :893-914

[7]

KRAPCHO AP, 1982, SYNTHESIS-STUTTGART, P805

[8] Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters [J].

Kuwano, R ;

Kondo, Y ;

Matsuyama, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12104-12105

[9] PALLADIUM-CATALYZED SUBSTITUTION OF ESTERS OF NAPHTHYLMETHANOLS, 1-NAPHTHYLETHANOLS, AND ANALOGS BY SODIUM DIMETHYL MALONATE - STEREOSELECTIVE SYNTHESIS FROM ENANTIOMERICALLY PURE SUBSTRATES [J].

LEGROS, JY ;

TOFFANO, M ;

FIAUD, JC .

TETRAHEDRON, 1995, 51 (11) :3235-3246

[10] PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF NAPHTHYLMETHYL AND 1-NAPHTHYLETHYL ESTERS [J].

LEGROS, JY ;

FIAUD, JC .

TETRAHEDRON LETTERS, 1992, 33 (18) :2509-2510

← 1 2 →