Exploiting differences in solution vs solid supported reactivity for the synthesis of sulfonic acid derivatives

被引：11

作者：

Hari, A ^{[1
]}

Miller, BL ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 13期

关键词：

D O I：

10.1021/ol991163z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a method herein for the protection of aryl and alkyl sulfonates during synthesis which employs commercially available Wang or MBOH resin, both of which terminate as benzyl alcohols, as both a protecting group and "traceless" linker. Given the known instability of benzylic sulfonate esters to nucleophilic displacement in solution, this linkage is surprisingly stable: no loss of either aryl or alkyl sulfonates is observed when the resin is exposed to a wide variety of organic bases and solvents at room temperature. Further elaboration of the resin-bound sulfonates via Suzuki coupling is also described.

引用

页码：2109 / 2111

页数：3

共 22 条

[1] KINETIC ISOTOPE EFFECTS IN THE MENSCHUTKIN-TYPE REACTION OF BENZYL BENZENESULFONATES WITH N,N-DIMETHYLANILINES - VARIATION IN THE TRANSITION-STATE STRUCTURE [J].