A mild and chemoselective method for the reduction of conjugated isoxazolines to β-hydroxy ketones

被引：93

作者：

Bode, JW ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 10期

关键词：

D O I：

10.1021/ol015885d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new procedure for the selective reduction of conjugated Delta (2)-isoxazolines to the corresponding unsaturated beta -hydroxy ketones is described. The use of SmI2 as the reducing agent and B(OH)(3) to hydrolyze the resulting imine results in a mild, convenient, and chemoselective protocol for this otherwise difficult transformation and complements existing methodology for the preparation of beta -hydroxy ketones via nitrile oxides.

引用

页码：1587 / 1590

页数：4

共 14 条

[1] SILYL NITRONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 3(H-2)-FURANONES
ANDERSEN, SH
SHARMA, KK
TORSSELL, KBG
[J]. TETRAHEDRON, 1983, 39 (13) : 2241 - 2245
[2] BARALDI PG, 1987, SYNTHESIS-STUTTGART, P276
[3] Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition
Bode, JW
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) : 3611 - 3612
[4] BODE JW, 2001, IN PRESS ANGEW CHEM, V40
[5] Cleavage of N-O bonds promoted by samarium diiodide: Reduction of free or N-acylated O-alkylhydroxylamines
Chiara, JL
Destabel, C
Gallego, P
MarcoContelles, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 359 - 360
[6] REDUCTION OF DELTA-2-ISOXAZOLINES .3. RANEY-NICKEL CATALYZED FORMATION OF BETA-HYDROXY KETONES
CURRAN, DP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) : 5826 - 5833
[7] REDUCTION OF SUBSTITUTED DELTA-2-ISOXAZOLINES - SYNTHESIS OF BETA-HYDROXY ACID-DERIVATIVES
CURRAN, DP
SCANGA, SA
FENK, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) : 3474 - 3478
[8] CURRAN DP, 1988, ADV CYCLOADDITION, V1, P129
[9] REACTIONS WITH ALPHA,BETA-UNSATURATED NITRILE OXIDES - SYNTHETIC STUDIES IN THE TERPENE FIELD - SYNTHESIS OF TAGETONES, OCIMENONES, DEODARONE AND ATLANTONE
ISAGER, P
THOMSEN, I
TORSSELL, KBG
[J]. ACTA CHEMICA SCANDINAVICA, 1990, 44 (08): : 806 - 813
[10] JAGER V, 1983, B SOC CHIM BELG, V92, P1039

← 1 2 →