Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives
Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives
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DOI：
10.1021/jo0156823
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发表时间：
2001-08-10
影响因子：
3.6
通讯作者：
Kurth, MJ
中科院分区：
文献类型：
--
作者：
Cheng, WC;Olmstead, MM;Kurth, MJ
介绍了采用无迹固相砜连接剂制备功能化4,5,6,7-四氢异吲哚的方法。从聚合物结合的3-（苯基磺酰基）- 3-亚砜(7)中热熔挤出SO2，原位生成聚合物结合的2-（苯基磺酰基）-1,3-丁二烯(9)，并与各种亲二酚进行Diels-Alder环加成，得到乙烯基砜树脂10-14。为了完成无迹连接体裂解策略，（对苯基磺酰基）甲基异氰化物或异氰乙酸乙酯与乙烯基砜部分反应，释放功能化。树脂的4,5,6,7-四氢异吲哚产物。利用这种化学反应，以聚苯乙烯/亚磺酸二乙烯基苯为原料，以32-41%的总收率制备了9个四氢异吲哚衍生物（6,15 -22.）。
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.