Solid phase synthesis of diverse isoxazolidines via 1,3-dipolar cycloaddition

被引：32

作者：

Haap, WJ ^{[1
]}

Kaiser, D ^{[1
]}

Walk, TB ^{[1
]}

Jung, G ^{[1
]}

机构：

[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(98)00099-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diverse substituted isoxazolidines 2-4 are assembled on solid phase by condensing hydroxylamines with aldehydes and trapping the resulting nitrones with various dipolarophiles. The one-pot three-component cycloaddition reaction yields the isoxazolidines in good to excellent yield. Three different reaction pathways - each dealing with one of the three components attached to the solid support - are evaluated with respect to versatility and yield of the synthesized isoxazolidines. Structures and relative configurations of representative isoxazolidines are elucidated with H-1-NMR, TOCSY, HSQC and NOESY. The reaction of polymer-bound hydroxylamines with aldehydes and alkenes is found to be the most successful. The kinetics of the solid phase reaction are determined by FT-IR-ATR spectroscopy. polymer-bound nitrones are stable for the split/combine synthesis. A library of isoxazolidines is synthesized by the split/combine method and analyzed by means of HPLC-MS. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3705 / 3724

页数：20

共 19 条

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