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

[11] Acid-catalyzed addition of N-hydroxyurea to 1-aryl alcohol derivatives:: A new synthesis of Zileuton [J].

Copp, RR ;

Fohey, BT ;

Lannoye, G .

SYNTHETIC COMMUNICATIONS, 2001, 31 (20) :3081-3086

[12]

DANIEL A, 1971, B SOC CHIM FR, P1060

[13] Phospho-transfer catalysis - On the asymmetric hydrophosphonylation of aldehydes [J].

Davies, SR ;

Mitchell, MC ;

Cain, CP ;

Devitt, PG ;

Taylor, RJ ;

Kee, TP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 550 (1-2) :29-57

[14] THE PREPARATION AND PROPERTIES OF 2-VINYLBENZOFURAN [J].

ELLIOTT, ED .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (02) :754-754

[15] RESOLUTION OF HYDROXYUREAS [J].

GARIGIPATI, RS ;

SORENSON, ME ;

ERHARD, KF ;

ADAMS, JL .

TETRAHEDRON LETTERS, 1993, 34 (35) :5537-5540

[16] 1-magnesiotetrahydroisoquinolyloxazolines as chiral nucleophiles in stereoselective additions to aldehydes: Auxiliary optimization, asymmetric synthesis of (+)-corlumine, (+)-bicuculline, (+)-egenine, and (+)-corytensine, and preliminary C-13 NMR studies of 1-lithio- and 1-magnesiotetrahydroisoquinolyloxazolines [J].

Gawley, RE ;

Zhang, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8103-8112

[17] Stereoselective carbon-carbon bond formation via the mitsunobu displacement of chiral secondary benzylic alcohols [J].

Hillier, MC ;

Desrosiers, JN ;

Marcoux, JF ;

Grabowski, EJJ .

ORGANIC LETTERS, 2004, 6 (04) :573-576

[18] A PRACTICAL SYNTHESIS OF 2-CARBONYLBENZO[B]THIOPHENES [J].

HSIAO, CN ;

BHAGAVATULA, L ;

PARIZA, RJ .

SYNTHETIC COMMUNICATIONS, 1990, 20 (11) :1687-1695

[19] SYNTHESIS OF CHIRAL ZILEUTON, A POTENT AND SELECTIVE INHIBITOR OF 5-LIPOXYGENASE [J].

HSIAO, CN ;

KOLASA, T .

TETRAHEDRON LETTERS, 1992, 33 (19) :2629-2632

[20] The Mitsunobu reaction of ortho-ethers of secondary benzylic alcohols. Concise enantioselective synthesis of a key intermediate of the novel beta-adrenergic receptor antagonist MY336-a [J].

Kaufman, TS .

TETRAHEDRON LETTERS, 1996, 37 (30) :5329-5332

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