Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives

被引：36

作者：

Cheng, WC ^{[1
]}

Olmstead, MM ^{[1
]}

Kurth, MJ ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 16期

关键词：

D O I：

10.1021/jo0156823

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of functionalized 4,5,6,7-tetrahydroisoindole via a traceless solid-phase sulfone linker strategy is described. Thermolytic extrusion Of SO2 from polymer-bound 3-(phenylsulfonyl)3-sulfolene (7) generated polymer-bound 2-(phenylsulfonyl)-1,3-butadiene (9) in situ which underwent Diels-Alder cycloaddition with various dienophiles to furnish vinyl sulfone resins 10-14, To complete a traceless linker cleavage strategy, (p-tolysulfonyl)methyl isocyanide or ethyl isocyanoacetate was employed to react with the vinyl sulfone moiety to liberate functionalized. 4,5,6,7-tetrahydroisoindole products from the resin. Using this chemistry, nine tetrahydroisoindole derivatives (6, 15-22.) were prepared in 32-41% overall yields from polystyrene/divinylbenzene sulfinate 1.

引用

页码：5528 / 5533

页数：6

共 42 条

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