Asymmetric synthesis of N-1-(heteroaryl)ethyl-N-hydroxyureas

被引：30

作者：

Bosiak, Mariusz J. ^{[1
]}

Krzeminski, Marek P. ^{[1
]}

Jaisankar, Parasuraman ^{[2
]}

Zaidlewicz, Marek ^{[1
]}

机构：

[1] Nicholas Copernicus Univ, Dept Chem, PL-87100 Torun, Poland

[2] Indian Inst Chem Biol, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 08期

关键词：

D O I：

10.1016/j.tetasy.2008.03.026

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric synthesis of two 5-lipoxygenase inhibitors (R)-N-1-(benzofuran-2-yl)ethyl-AT-hydroxyurea, 99% ee, and (R)N-1-(benzo [b]thiophen-2-yl)ethyl-N-hydroxyurea, 95% ee, is described. The enantioselective reduction of 1-(benzofuran-2-yl)ethanone oxime O-benzyl ether and 1-(benzo[b]thiophen-2-yl)ethanone oxime O-benzyl ether with borane oxazaborolidine, generated from (1R,2S,3R,4S)-3-amino-1, 7,7-trimethylbicyclo [2.2.1]heptan-2-ol, was used for the formation of the stereogenic centres. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：956 / 963

页数：8

共 39 条

[1]

Balkan Ayla, 2003, Current Medicinal Chemistry - Anti-Inflammatory & Anti-Allergy Agents, V2, P9, DOI 10.2174/1568014033355853

[2] ADDITION OF ORGANOMETALLIC REAGENTS TO N-GLYCOSYL NITRONES - ENANTIOSELECTIVE SYNTHESES OF (+)-(R)-ZILEUTON AND (-)-(S)-ZILEUTON [J].

BASHA, A ;

HENRY, R ;

MCLAUGHLIN, MA ;

RATAJCZYK, JD ;

WITTENBERGER, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :6103-6106

[3] ADDITION OF ORGANOLITHIUM COMPOUNDS TO N-THP PROTECTED NITRONE [J].

BASHA, A ;

RATAJCZYK, JD ;

BROOKS, DW .

TETRAHEDRON LETTERS, 1991, 32 (31) :3783-3786

[4] STEREOCHEMISTRY OF 2-HYDROXY-3-AMINOBORNANES [J].

BECKETT, AH ;

LAN, NT ;

MCDONOUGH, GR .

TETRAHEDRON, 1969, 25 (23) :5689-+

[5] ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].

BONNER, MP ;

THORNTON, ER .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308

[6]

Brooks D. W., 1995, SEARCH ANTIINFLAMMAT, P129

[7]

BROOKS DW, 1995, J MED CHEM, V39, P4768

[8] BENZO[B]THIOPHEN DERIVATIVES .11. NITRATION OF 3-ACETYL-BENZO[B]THIOPHENS AND 3-FORMYL-BENZO[B]THIOPHENS [J].

BROPHY, GC ;

MARTINSM.M ;

STERNHEL.S ;

BROWN, NMD ;

BROWN, I ;

ARMSTRON.KJ .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (07) :933-+

[9] Alternative synthetic route to chiral N-substituted camphor-derived β-amino alcohols [J].

Cheng, Gin-Ian ;

Shei, Chun-Tin ;

Sung, Kuangsen .

CHIRALITY, 2007, 19 (03) :235-238

[10] AMINOBICYCLO2,2,1!HEPTANES .2. DIASTEREOISOMERIC DIMETHYLAMINOBORNYL ACETATES [J].

CHITTENDEN, RA ;

COOPER, GH .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (01) :49-+

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