Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis

被引:73
作者
Kroll, FEK
Morphy, R
Rees, D
Gani, D
机构
[1] UNIV ST ANDREWS,SCH CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND
[2] UNIV ST ANDREWS,CTR BIOMOL SCI,ST ANDREWS KY16 9ST,FIFE,SCOTLAND
[3] ORGANON LABS,DEPT MED CHEM,NEWHOUSE ML1 5SH,LANARK,SCOTLAND
基金
英国惠康基金;
关键词
D O I
10.1016/S0040-4039(97)10291-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New polystyrene-based resins containing benzyl and aryl vinyl sulfone groups are described. The vinyl sulfone group reacts efficiently with 2 degrees amines, via conjugate addition, and the resin-bound 3 degrees amine products can be quaternised through alkylation. Subsequent deamination to give 3 degrees amines and the regenerated vinyl sulfone occurs in moderate to good yield. Both systems can be recycled and show moderate stability to acids and high stability to nucleophiles including Grignard reagents. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8573 / 8576
页数:4
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