Synthesis of new pyridyl alcohols and their use as catalysts in the asymmetric addition of diethylzinc to aldehydes

被引：30

作者：

Xu, QY

Wu, XM

Pan, XF ^{[1
]}

Chan, ASC

Yang, TK

机构：

[1] Lanzhou Univ, Dept Chem, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China

[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

[4] Natl Chunghsing Univ, Dept Chem, Taichung 40227, Taiwan

来源：

CHIRALITY | 2002年 / 14卷 / 01期

关键词：

asymmetric addition; pyridyl alcohols; (+)-camphor; (-)-menthone; diethylzinc;

D O I：

10.1002/chir.10027

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Optically active new pyridyl alcohols 1-4, which can be easily synthesized by the reaction of (+)-camphor or (-)-menthone with lithiated pyridine derivatives, were applied as chiral ligands in the asymmetric addition of diethylzinc to aldehydes. Good yields with up to 94.0% enantiomeric excesses were observed in these reactions. (C) 2002 Wiley-Liss. Inc.

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页码：28 / 31

页数：4

相关论文

共 22 条

[1] LIGAND-ACCELERATED CATALYSIS [J].

BERRISFORD, DJ ;

BOLM, C ;

SHARPLESS, KB .

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

[2]

BEUMEL OF, 1974, SYNTHESIS-STUTTGART, P43

[3] CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].

BOLM, C ;

SCHLINGLOFF, G ;

HARMS, K .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1191-1203

[4]

CHO BT, 1994, TETRAHEDRON LETT, V35, P4115

[5] Synthesis of new enantiopure gamma-aminoalcohols: Their use as catalysts in the alkylation of benzaldehyde by diethylzinc [J].

Cicchi, S ;

Crea, S ;

Goti, A ;

Brandi, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :293-301

[6] Highly diastereoselective synthesis of new optically active aminoalcohols in one step from (+)-camphor and (-)-fenchone [J].

Genov, M ;

Kostova, K ;

Dimitrov, V .

TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1869-1876

[7] New delta-aminoalcohol for the enantioselective addition of dialkylzincs to aldehydes [J].

Genov, M ;

Dimitrov, V ;

Ivanova, V .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3703-3706

[8] Origin of enantioselectivities in chiral β-amino alcohol catalyzed asymmetric additions of organozinc reagents to benzaldehyde:: PM3 transition state modeling [J].

Goldfuss, B ;

Houk, KN .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8998-9006

[9] Enantioselective addition of diethylzinc to aldehydes catalyzed by optically active 1,4-aminoalcohols [J].

Hanyu, N ;

Aoki, T ;

Mino, T ;

Sakamoto, M ;

Fujita, T .

TETRAHEDRON-ASYMMETRY, 2000, 11 (14) :2971-2979

[10] Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs [J].

Kitamura, M ;

Suga, S ;

Oka, H ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9800-9809