Synthesis of (S)-(+)-sotalol and (R)-(-)-isoproterenol via a catalytic enantioselective Henry reaction

被引：47

作者：

Blay, Gonzalo ^{[1
]}

Hernandez-Olmos, Victor ^{[1
]}

Pedro, Jose R. ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Burjassot, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 05期

关键词：

PERFORMANCE LIQUID-CHROMATOGRAPHY; INDUCED MYOCARDIAL INJURY; BETA-ADRENERGIC BLOCKERS; D-SOTALOL; COPPER(II)-IMINOPYRIDINE COMPLEXES; ASYMMETRIC-SYNTHESIS; RESOLUTION; ISOPROTERENOL; DRUGS; DERIVATIZATION;

D O I：

10.1016/j.tetasy.2010.02.027

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A unified approach for the synthesis of (S)-(+)-sotalol and (R)-(-)-isoproterenol has been developed. The enantioselective Henry reaction of the appropriate aldehyde in the presence of a camphor-derived amino pyridine-Cu(II) complex was the key step of the synthesis. The reduction of the nitro group to give the corresponding amino alcohols followed by reductive alkylation of the amine provided the target products with high enantiomeric excesses. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：578 / 581

页数：4

共 52 条

[1] Enantioselective synthesis of epoxides and aziridines by asymmetric methylidene transfer from a sulfimide to carbonyl compounds and imines [J].

Baird, CP ;

Taylor, PC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (20) :3399-3403

[2] RESOLUTION OF ISOPROPYL NOR-ADRENALINE INTO OPTICAL ISOMERS AND THEIR PHARMACOLOGICAL POTENCY RATIO [J].

BECCARI, E ;

BERETTA, A ;

LAWENDEL, JS .

SCIENCE, 1953, 118 (3061) :249-250

[3] SELECTIVE REDUCTION OF AROMATIC NITRO-COMPOUNDS WITH STANNOUS CHLORIDE IN NON-ACIDIC AND NON-AQUEOUS MEDIUM [J].

BELLAMY, FD ;

OU, K .

TETRAHEDRON LETTERS, 1984, 25 (08) :839-842

[4] COMPARATIVE EFFECTS OF D-SOTALOL AND L-SOTALOL ON THE ATRIOVENTRICULAR NODE OF THE RABBIT HEART [J].

BEYER, T ;

BRACHMANN, J ;

KUBLER, W .

JOURNAL OF CARDIOVASCULAR PHARMACOLOGY, 1993, 22 (02) :240-246

[5] A catalytic highly enantioselective direct synthesis of 2-bromo-2-nitroalkan-1-ols through a Henry reaction [J].

Blay, Gonzalo ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

CHEMICAL COMMUNICATIONS, 2008, (39) :4840-4842

[6] New highly asymmetric henry reaction catalyzed by CuII and a C1-Symmetric aminopyridine ligand, and its application to the synthesis of miconazole [J].

Blay, Gonzalo ;

Domingo, Luis R. ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (15) :4725-4730

[7] Enantioselective addition of nitromethane to α-keto esters catalyzed by copper(II)-iminopyridine complexes [J].

Blay, Gonzalo ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (03) :468-476

[8] Enantioselective Henry reaction catalyzed with copper(II)-iminopyridine complexes [J].

Blay, Gonzalo ;

Climent, Estela ;

Fernandez, Isabel ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (13) :1603-1612

[9] Modular iminopyridine ligands.: Application to the enantioselective copper(II)-catalyzed Henry reaction [J].

Blay, Gonzalo ;

Climent, Estela ;

Fernandez, Isabel ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (14) :2046-2049

[10]

Brittain R T, 1970, Adv Drug Res, V5, P197

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