The reversed Kenner linker:: A new safety-catch linker for the preparation of N-alkyl sulfonamides

被引：34

作者：

Maclean, D ^{[1
]}

Hale, R ^{[1
]}

Chen, MY ^{[1
]}

机构：

[1] Affymax Res Inst, Palo Alto, CA 94304 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 19期

关键词：

D O I：

10.1021/ol0163124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new strategy for the solid-phase synthesis of sulfonamides is described. The Kenner safety-catch strategy has been modified such that the carboxylic acid component remains attached to the solid support while the sulfonamide portion is released into solution. An initial demonstration of the scope of this strategy is presented, along with an analysis of the cleavage characteristics and extension to more elaborate products via Suzuki reaction and thiazolidinone synthesis.

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页码：2977 / 2980

页数：4

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共 24 条

[1] Chiral N-acyl-tert-butanesulfinamides:: The "safety-catch" principle applied to diastereoselective enolate alkylations [J].

Backes, BJ ;

Dragoli, DR ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5472-5478

[2] Activation method to prepare a highly reactive acylsulfonamide ''safety-catch'' linker for solid-phase synthesis [J].

Backes, BJ ;

Virgilio, AA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3055-3056

[3] CARBON-CARBON BOND-FORMING METHODS ON SOLID SUPPORT - UTILIZATION OF KENNER SAFETY-CATCH LINKER [J].

BACKES, BJ ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11171-11172

[4] Solid support linker strategies [J].

Backes, BJ ;

Ellman, JA .

CURRENT OPINION IN CHEMICAL BIOLOGY, 1997, 1 (01) :86-93

[5] An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].

Backes, BJ ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330

[6] Application of the sulfonamide functional group as an anchor for solid phase organic synthesis (SPOS) [J].

Beaver, KA ;

Siegmund, AC ;

Spear, KL .

TETRAHEDRON LETTERS, 1996, 37 (08) :1145-1148

[7] AMEBA: An acid sensitive aldehyde resin for solid phase synthesis [J].

Fivush, AM ;

Willson, TM .

TETRAHEDRON LETTERS, 1997, 38 (41) :7151-7154

[8] The Suzuki, the Heck, and the Stille reaction -: three versatile methods for the introduction of new C-C bonds on solid support [J].

Franzén, R .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2000, 78 (07) :957-962

[9] Biotin labelling of amines by polymer-assisted solution-phase synthesis [J].

Golisade, A ;

Herforth, C ;

Wieking, K ;

Kunick, C ;

Link, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1783-1786

[10] STRATEGIES FOR COMBINATORIAL ORGANIC-SYNTHESIS - SOLUTION AND POLYMER-SUPPORTED SYNTHESIS OF 4-THIAZOLIDINONES AND 4-METATHIAZANONES DERIVED FROM AMINO-ACIDS [J].

HOLMES, CP ;

CHINN, JP ;

LOOK, GC ;

GORDON, EM ;

GALLOP, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7328-7333