The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes

被引：125

作者：

Liu, DX

Zhang, LC

Wang, Q

Da, CS

Xin, ZQ

Wang, R ^{[1
]}

Choi, MCK

Chan, ASC

机构：

[1] Lanzhou Univ, Dept Biochem & Mol Biol, Open Lab Chirotechnol, Sch Life Sci, Lanzhou 730000, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 17期

关键词：

D O I：

10.1021/ol016341e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Optically active aminonaphthol 3 obtained by condensation of 2-naphthol, benzaldehyde, and (S)-methylbenzylamine followed by N-methylation was found to catalyze the enantioselective ethylation of aryl aldehydes to secondary alcohols with high enantioselectivities (up to 99.8%) at room temperature.

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收藏

页码：2733 / 2735

页数：3

相关论文

共 29 条

[1] The importance of nitrogen substituents in chiral amino thiol ligands for the asymmetric addition of diethylzinc to aromatic aldehydes [J].

Anderson, JC ;

Harding, M .

CHEMICAL COMMUNICATIONS, 1998, (03) :393-394

[2] OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS [J].

BOLM, C ;

ZEHNDER, M ;

BUR, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02) :205-207

[3] Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [J].

Bringmann, G ;

Breuning, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (04) :667-679

[4] Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes [J].

Cardellicchio, C ;

Ciccarella, G ;

Naso, F ;

Perna, F ;

Tortorella, P .

TETRAHEDRON, 1999, 55 (51) :14685-14692

[5] Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes [J].

Chan, ASC ;

Zhang, FY ;

Yip, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :4080-4081

[6] CHIRAL LIGANDS CONTAINING HETEROATOMS .8. 2-[(2S)-2-PYRROLIDINYL]PYRIDINE AS A NOVEL CATALYST IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].

CHELUCCI, G ;

CONTI, S ;

FALORNI, M ;

GIACOMELLI, G .

TETRAHEDRON, 1991, 47 (38) :8251-8258

[7] Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol [J].

Cho, BT ;

Chun, YS .

TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1489-1492

[8] CHIRAL LIGANDS CONTAINING HETEROATOMS .10. 1-(2-PYRIDYL)ALKYLAMINES AS CHIRAL CATALYSTS IN THE ADDITION OF DIETHYLZINC TO ALDEHYDES - TEMPERATURE-DEPENDENCE ON THE ENANTIOSELECTIVITY [J].

CONTI, S ;

FALORNI, M ;

GIACOMELLI, G ;

SOCCOLINI, F .

TETRAHEDRON, 1992, 48 (41) :8993-9000

[9]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[10]

2-V