Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction

被引：74

作者：

Chemler, SR

Danishefsky, SJ

机构：

[1] Sloan Kettering Inst Canc Res, Dept Bioorgan Chem, New York, NY 10021 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 17期

关键词：

D O I：

10.1021/ol0062547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TIOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.

引用

页码：2695 / 2698

页数：4