Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis
作者:Friedrich E.K. Kroll、Richard Morphy、David Rees、David Gani
DOI:10.1016/s0040-4039(97)10291-x
日期:1997.12
New polystyrene-based resins containing benzyl and aryl vinyl sulfone groups are described. The vinyl sulfone group reacts efficiently with 2° amines, via conjugate addition, and the resin-bound 3° amine products can be quatermised through alkylation. Subsequent deamination to give 3° amines and the regenerated vinyl sulfone occurs in moderate to good yield. Both systems can be recycled and show moderate
描述了含有苄基和芳基乙烯基砜基团的新型聚苯乙烯基树脂。乙烯基砜基团通过共轭加成与2°胺有效反应,与树脂结合的3°胺产物可通过烷基化进行季铵化。随后的脱氨基反应得到3°胺,再生的乙烯基砜以中等至良好的收率发生。两种系统均可循环使用,对酸显示出中等稳定性,对包括格氏试剂在内的亲核试剂显示出高稳定性。