ZrCl4 as an efficient catalyst for a novel one-pot protection/deprotection synthetic methodology

被引：35

作者：

Singh, Surendra ^{[1
]}

Duffy, Colm D. ^{[1
]}

Shah, Syed Tasadaque A. ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, UCD Conway Inst, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo800932t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic quantity of ZrCl4 (20 mol %) was found to be an efficient catalyst for the one-pot esterification and deprotection of (5S,6R)-5,6-diacetoxyoct-7-enoic acid in good yields (44-62%) with a lactone formed as a minor byproduct. ZrCl4 (10-20 mol %) was also sufficient to deprotect 1,3-dioxalane, bis-TBDMS ethers, and diacetate functional groups in excellent yields of up to 93%. ZrCl4 (1-10 mol %) also promoted diol protection as the acetonide in 90% yield and acted as a trans-esterification catalyst for a range of esters.

引用

页码：6429 / 6432

页数：4