Asymmetric palladium-catalyzed nucleophilic substitution of 1-(2-naphthyl)ethyl acetate by dimethyl malonate anion

被引:28
作者
Legros, JY [1 ]
Boutros, A [1 ]
Fiaud, JC [1 ]
Toffano, M [1 ]
机构
[1] Univ Paris 11, CNRS, UPRESA 8075,Lab Catalyse Mol Associe, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France
关键词
palladium; asymmetric catalysis; benzylic nucleophilic substitution; C-C bond formation; elimination;
D O I
10.1016/S1381-1169(02)00631-3
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The asymmetric palladium-catalyzed nucleophilic substitution of 1-(2-naphthyl)ethyl acetate (1) by dimethyl malonate anion was realized and led to dimethyl 2-[1-(2-naphthyl)ethyl]propanedioate (2) with up to 74% ee. The analysis of the course of the reaction gave some information on the behaviour of the intermediate complexes. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:21 / 25
页数:5
相关论文
共 10 条
[1]   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
[2]   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
[3]   IDENTIFICATION OF THE ENANTIOSELECTIVE STEP IN THE ASYMMETRIC CATALYTIC-HYDROGENATION OF A PROCHIRAL OLEFIN [J].
CHAN, ASC ;
PLUTH, JJ ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5952-5954
[4]   NEW METHOD FOR THE CLASSIFICATION OF NUCLEOPHILES IN THE PALLADIUM-CATALYZED SUBSTITUTION OF ALLYLIC ACETATES [J].
FIAUD, JC ;
LEGROS, JY .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :1907-1911
[5]   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
[6]   PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF NAPHTHYLMETHYL AND 1-NAPHTHYLETHYL ESTERS [J].
LEGROS, JY ;
FIAUD, JC .
TETRAHEDRON LETTERS, 1992, 33 (18) :2509-2510
[7]   ASYMMETRIC PALLADIUM-CATALYZED NUCLEOPHILIC-SUBSTITUTION OF RACEMIC 1-NAPHTHYLETHYL ESTERS [J].
LEGROS, JY ;
TOFFANO, M ;
FIAUD, JC .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1899-1902
[8]   Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution [J].
Legros, JY ;
Primault, G ;
Toffano, M ;
Rivière, MA ;
Fiaud, JC .
ORGANIC LETTERS, 2000, 2 (04) :433-436
[9]   ASYMMETRIC-SYNTHESIS - MECHANISM OF ASYMMETRIC CATALYTIC ALLYLATION [J].
MACKENZIE, PB ;
WHELAN, J ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2046-2054
[10]   DMF as a dimethylamine equivalent in the palladium-catalyzed nucleophilic substitution of naphthylmethyl and allyl acetates [J].
Toffano, M ;
Legros, JY ;
Fiaud, JC .
TETRAHEDRON LETTERS, 1997, 38 (01) :77-80