A radical approach to N-desulfonylation

被引：65

作者：

Parsons, AF

Pettifer, RM

机构：

[1] Department of Chemistry, University of York, Heslington, York

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 10期

关键词：

D O I：

10.1016/0040-4039(96)00086-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The deprotection of N-sulfonylated amides can be achieved under neutral conditions by reaction with tributyltin hydride. Good yields are obtained using N-benzoyl and related amides while the corresponding N-acetyl derivatives are inert under the same reaction conditions. The mechanistic implications of this are discussed.

引用

收藏

页码：1667 / 1670

页数：4

相关论文

共 17 条

[1] OXIDATIVE RADICAL CYCLIZATION TO PYRROLES UNDER REDUCING CONDITIONS - REDUCTIVE DESULFONYLATION OF ALPHA-SULFONYLPYRROLES WITH TRI-N-BUTYLTIN HYDRIDE [J].

ANTONIO, Y ;

DELACRUZ, ME ;

GALEAZZI, E ;

GUZMAN, A ;

BRAY, BL ;

GREENHOUSE, R ;

KURZ, LJ ;

LUSTIG, DA ;

MADDOX, ML ;

MUCHOWSKI, JM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01) :15-22

[2] 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

[3]

Du Vigneaud V, 1937, J BIOL CHEM, V117, P27

[4]

GAJDA T, 1981, SYNTHESIS-STUTTGART, P1005

[5] PROTECTION OF AMINES BY THE PYRIDINE-2-SULFONYL GROUP AND ITS CLEAVAGE UNDER MILD CONDITIONS (SMI2 OR ELECTROLYSIS) [J].

GOULAOUICDUBOIS, C ;

GUGGISBERG, A ;

HESSE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5969-5972

[6]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[7] MODERN METHODS FOR THE RADICAL DEOXYGENATION OF ALCOHOLS [J].

HARTWIG, W .

TETRAHEDRON, 1983, 39 (16) :2609-2645

[8] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES [J].

HENRY, JR ;

MARCIN, LR ;

MCINTOSH, MC ;

SCOLA, PM ;

HARRIS, GD ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1989, 30 (42) :5709-5712

[9] CHIRAL INDUCTION IN ARYL RADICAL CYCLIZATIONS [J].

JONES, K ;

MCCARTHY, C .

TETRAHEDRON LETTERS, 1989, 30 (20) :2657-2660

[10]

KHOO LE, 1968, TETRAHEDRON LETT, P4351