Samarium(II) iodide reduction of isoxazolidines

被引：55

作者：

Revuelta, J ^{[1
]}

Cicchi, S ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, Polo Sci, I-50019 Sesto Fiorentino, Italy

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 45期

关键词：

samarium iodide; reduction; isoxazolidine;

D O I：

10.1016/j.tetlet.2004.09.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SmI2 was used as reducing agent for the N-O bond cleavage in isoxazolidines. The procedure revealed is general and particularly useful for the transformation of 5-spirocyclopropane isoxazolidines to the corresponding beta-aminocyclopropanols, a troublesome transformation with other known reagents. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8375 / 8377

页数：3

共 33 条

[1] STEREOSELECTIVE TOTAL SYNTHESES OF (+/-)-SINULARENE AND (+/-)-5-EPI-SINULARENE - A GENERAL INTRAMOLECULAR DIELS-ALDER APPROACH TO TRICYCLIC SESQUITERPENES [J].

ANTCZAK, K ;

KINGSTON, JF ;

FALLIS, AG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (04) :993-995

[2] SAMARIUM(II) IODIDE PROMOTED RADICAL RING-OPENING REACTIONS OF CYCLOPROPYL KETONES [J].

BATEY, RA ;

MOTHERWELL, WB .

TETRAHEDRON LETTERS, 1991, 32 (45) :6649-6652

[3] STEREOELECTRONIC CONTROL IN THE REDUCTIVE OPENING OF CYCLOPROPYLOGOUS ALPHA-HALOKETONES [J].

BEERLI, R ;

BRUNNER, EJ ;

BORSCHBERG, HJ .

TETRAHEDRON LETTERS, 1992, 33 (43) :6449-6452

[4] New samarium diiodide-induced ketyl couplings -: From analogous reactions to serendipitously discovered processes [J].

Berndt, M ;

Gross, S ;

Hölemann, A ;

Reissig, HU .

SYNLETT, 2004, (03) :422-438

[5] A mild and chemoselective method for the reduction of conjugated isoxazolines to β-hydroxy ketones [J].

Bode, JW ;

Carreira, EM .

ORGANIC LETTERS, 2001, 3 (10) :1587-1590

[6] Heterocycles from alkylidenecyclopropanes [J].

Brandi, A ;

Cicchi, S ;

Cordero, FM ;

Goti, A .

CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269

[7] Domino palladium(II)-mediated rearrangement-oxidative cyclization of β-aminocyclopropanols [J].

Cicchi, S ;

Revuelta, J ;

Zanobini, A ;

Betti, M ;

Brandi, A .

SYNLETT, 2003, (15) :2305-2308

[8] Indium-mediated reduction of hydroxylamines to amines [J].

Cicchi, S ;

Bonanni, M ;

Cardona, F ;

Revuelta, J ;

Goti, A .

ORGANIC LETTERS, 2003, 5 (10) :1773-1776

[9] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].

CICCHI, S ;

GOTI, A ;

BRANDI, A ;

GUARNA, A ;

DESARLO, F .

TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354

[10] A convenient synthesis of iminosugar-C-glycosides via organometallic addition to N-benzyl-N-glycosylhydroxylamines [J].

Dondoni, A ;

Perrone, D .

TETRAHEDRON, 2003, 59 (24) :4261-4273

← 1 2 3 4 →