Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(IV) complexes of C2-symmetrical chiral BINOL derivatives

被引：32

作者：

Gou, Shaohua ^{[1
]}

Judeh, Zaher M. A. ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, Singapore 637459, Singapore

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 03期

关键词：

Aldehyde; Alkylation; BINOL; Diethylzinc; Secondary alcohol; Ti(OiPr)(4); Chiral core; Chiral C-2-symmetric ligand; BAYLIS-HILLMAN REACTION; CARBONYL-COMPOUNDS; LIGANDS; AMPLIFICATION; TITANIUM(IV); BINAPHTHOL; REAGENTS; BASE;

D O I：

10.1016/j.tetlet.2008.10.149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective addition of diethylzinc to a series of aromatic aldehydes is developed using new chiral C2-symmetric ligand (S)-2,2'-(1,1'-binaphthyl-2,2'-diylbis(oxy))bis(methylene)bis(4-nitrophenol) (S)-2b. The catalytic system employing 10 mol % of (S)-2b and 120 mot %. of Ti(OiPr)(4) was found to promote the addition of diethylzinc to a wide range of aromatic aldehydes with electron-donating and electron-withdrawing substituents, giving up to 89% ee and up to 95% yield of the corresponding secondary alcohol under mild conditions. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：281 / 283

页数：3

共 26 条

[1] Enantioselective diethylzinc addition to aldehydes catalyzed by Ti(IV) complex of unsymmetrical chiral bis(sulfonamide) ligands of trans-cyclohexane 1,2-diamine [J].

Bisai, Alakesh ;

Singh, Pradeep K. ;

Singh, Vinod K. .

TETRAHEDRON, 2007, 63 (03) :598-601

[2] Tailoring the ligand structure to the reagent in the mandelamide-Ti (IV) catalyzed enantioselective addition of dimethyl- and diethylzinc to aldehydes [J].

Blay, Gonzalo ;

Fernandez, Isabel ;

Hernandez-Olmos, Victor ;

Marco-Aleixandre, Alicia ;

Pedro, Jose R. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 276 (1-2) :235-243

[3] BINOL: A versatile chiral reagent [J].

Brunel, JM .

CHEMICAL REVIEWS, 2005, 105 (03) :857-897

[4] Efficient chirality switching in the addition of diethylzinc to aldehydes in the presence of simple chiral α-amino amides [J].

Burguete, M. Isabel ;

Collado, Manuel ;

Escorihuela, Jorge ;

Luis, Santiago V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) :9002-9005

[5] Modified BINOL ligands in asymmetric catalysis [J].

Chen, Y ;

Yekta, S ;

Yudin, AK .

CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211

[6] Syntheses of novel chiral sulfinamido ligands and their applications in diethylzinc additions to aldehydes [J].

Huang, Zhiyan ;

Lai, Hongshan ;

Qin, Yong .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1373-1378

[7] Titanium(IV) as an essential promoter in the asymmetric addition of diethylzinc to aldehydes catalyzed by aminonaphthol and imme ligands based on 3-substituted binaphthol [J].

Jiang, Fu-Yong ;

Liu, Bing ;

Dong, Zhi-Bing ;

Li, Jin-Shan .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (20) :4377-4380

[8]

JOSE ED, 2008, TETRAHEDRON-ASYMMETR, V19, P1250

[9] Chiral amplification based on enantioselective dual-phase distribution of a scalemic bisoxazolidine catalyst [J].

Liu, Shuanglong ;

Wolf, Christian .

ORGANIC LETTERS, 2007, 9 (16) :2965-2968

[10]

MANABU H, 2006, J ORG CHEM, V71, P6474

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