Intramolecular, reductive cyclization of β-ketoisothiocyanates promoted by using samarium diiodide

被引：7

作者：

Cho, MS ^{[1
]}

Lee, IS ^{[1
]}

Kang, SH ^{[1
]}

Kim, YH ^{[1
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 05期

关键词：

cyclization; diastereoselectivity; heterocycles; radical reactions; samarium;

D O I：

10.1002/chem.200400676

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel samarium diiodide (SmI2) promoted intramolecular cyclization of beta-ketoisothiocyanate, derived from alpha,beta-unsaturated esters and ammonium thiocyanate led to alpha-hydroxythiolactams and/or thiolactams in high yields. Treatment of beta-ketoisothiocyanate with two equivalents of SmI2 gave a mixture of alpha-hydroxythiolactam and thiolactam. Four equivalents of SmI2 afforded only thiolactam in high yields. The intramolecular cyclization took place with high to complete stereoselectivity. A mechanism to explain this transformation is proposed.

引用

页码：1452 / 1458

页数：7

共 44 条

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