Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing cinchonidine and cinchonine as chiral ligands

被引：22

作者：

Beresford, KJM ^{[1
]}

机构：

[1] De Montfort Univ, Fac Hlth & Life Sci, Leicester Sch Pharm, Leicester LE1 9BH, Leics, England

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 31期

关键词：

N-diphenylphosphinoylimine; cinchona alkaloids; diethylzinc; enantioselective addition; achiral additive;

D O I：

10.1016/j.tetlet.2004.06.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of the 'pseudoenantiomeric pair' of cinchonine and cinchonidine as ligands for the addition of diethylzinc to N-diphenylphosphinoylimines has been investigated. With 1 equiv of cinchonidine as ligand, a series of chiral amines was prepared in good yield and enantiomeric excesses of up to 94%. The use of 2.0 equiv of methanol as an achiral additive was found significantly to improve the selectivity of the addition when using 0.2 equiv of ligand, yielding ce's close to those obtained with a stoichiometric amount of ligand. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6041 / 6044

页数：4

共 14 条

[1] Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines [J].

Andersson, PG ;

Guijarro, D ;

Tanner, D .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7364-7375

[2] The use of achiral ligands to convey asymmetry: Chiral environment amplification [J].

Balsells, J ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1802-1803

[3] Enantioselective addition of diethylzinc to a N-diphenylphosphinoylimine employing cinchona alkaloids as chiral ligands [J].

Beresford, KJM .

TETRAHEDRON LETTERS, 2002, 43 (40) :7175-7177

[4] LIGAND-ACCELERATED CATALYSIS [J].

BERRISFORD, DJ ;

BOLM, C ;

SHARPLESS, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070

[5]

Jacques J., 1981, Enantiomers, Racemates and Resolutions

[6] THE TITANIUM TETRACHLORIDE INDUCED SYNTHESIS OF N-PHOSPHINOYLIMINES AND N-SULPHONYLIMINES DIRECTLY FROM AROMATIC-ALDEHYDES [J].

JENNINGS, WB ;

LOVELY, CJ .

TETRAHEDRON, 1991, 47 (29) :5561-5568

[7] Catalytic enantioselective addition to imines [J].

Kobayashi, S ;

Ishitani, H .

CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094

[8] THE INFLUENCE OF ATROPISOMERISM AND CHIRAL CENTER ON THE BIOLOGICAL-ACTIVITY OF METOLACHLOR [J].

MOSER, H ;

RIHS, G ;

SAUTER, H .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1982, 37 (04) :451-462

[9] Increased enantioselectivity in the addition of diethylzinc to benzaldehyde by the use of chiral ligands containing the α-phenylethylamino group in combination with achiral ligands [J].

Muñoz-Muñiz, O ;

Juaristi, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3781-3785

[10] Asymmetric addition of diethylzinc to N-(diphenylphosphinoyl) imines [J].

Pinho, P ;

Andersson, PG .

TETRAHEDRON, 2001, 57 (08) :1615-1618

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