Thioether-phosphinite and diphosphinite ligands derived from D-xylose for the copper-catalyzed asymmetric 1,4-addition to 2-cyclohexenone

被引：14

作者：

Guimet, E ^{[1
]}

Diéguez, M ^{[1
]}

Ruiz, A ^{[1
]}

Claver, C ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43007, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 12期

关键词：

D O I：

10.1016/j.tetasy.2005.05.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of thioether phosphinite 1-3 and diphosphinite 4 and 5 ligands. derived from inexpensive D-(+)-xylose, were tested for the first time in the Cu-catalyzed asyminetric 1,4-addition to 2-cyclohexenone 6. Good enantioselectivities (up to 72%) and activities [TOF up to > 1225 mol (mol h(-1))] combined with excellent selectivity in the 1,4 product were obtained. Our results show that activity and selectivity (chemo- and enantioselectivity) depend strongly on the type of functional group at the C-5 position of the carbohydrate backbone, the steric properties of the substittlent in the thioether moiety, the catalyst precursor and the alkylating agent. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2161 / 2165

页数：5

共 42 条

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Diéguez, M
Pàmies, O
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Ruiz, A
Claver, C
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 185 (1-2) : 11 - 16
[2] Copper-catalyzed highly enantioselective 1,4-conjugate addition of trimethylaluminum to 2-cyclohexenone
Liang, L
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TETRAHEDRON-ASYMMETRY, 2002, 13 (13) : 1393 - 1396
[3] Asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone catalyzed by Rh(I)/binap complexes
Takaya, Y
Ogasawara, M
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CHIRALITY, 2000, 12 (5-6) : 469 - 471
[4] Copper-catalysed asymmetric 1,4-addition of organometallic reagents to 2-cyclohexenone using novel phosphine-phosphite ligands
Diéguez, M
Deerenberg, S
Pàmies, O
Claver, C
van Leeuwen, PWNM
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TETRAHEDRON-ASYMMETRY, 2000, 11 (15) : 3161 - 3166
[5] New chiral amino-phosphite and phosphite-phosphoroamidite ligands for the copper-catalyzed asymmetric 1,4-addition of diethylzinc to cyclohexenone
Diéguez, M
Ruiz, A
Claver, C
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2861 - 2866
[6] Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to cyclohexenone: asymmetric induction as an unexpected source of structural information
Wendisch, V.
Sewald, N.
Tetrahedron: Asymmetry, 8 (08):
[7] Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to cyclohexenone: Asymmetric induction as an unexpected source of structural information
Wendisch, V
Sewald, N
TETRAHEDRON-ASYMMETRY, 1997, 8 (08) : 1253 - 1257
[8] Copper-Catalyzed 1,4-Addition of Organoboronates to Alkylidene Cyanoacetates: Mechanistic Insight and Application to Asymmetric Catalysis
Takatsu, Keishi
Shintani, Ryo
Hayashi, Tamio
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) : 5548 - 5552
[9] An insoluble polymer-bound phosphoramidite for the copper-catalysed enantioselective 1,4-addition of ZnEt2 to 2-cyclohexenone
Mandoli, A
Calamante, M
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TETRAHEDRON-ASYMMETRY, 2003, 14 (23) : 3647 - 3650
[10] Chiral diphosphites derived from D-glucose in the copper-catalyzed conjugate addition of diethylzinc to cyclohexenone
Diéguez, M
Ruiz, A
Claver, C
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2895 - 2900

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