Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers.

Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers.
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无环酯还原乙酰化的改进程序和醚的新合成。

DOI:
10.1021/jo9914521
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发表时间:
2000
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Rychnovsky,SD
Rychnovsky,SD
中科院分区:
--
文献类型:
--
作者:
Kopecky,DJ;Rychnovsky,SD

文献摘要

被引文献

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描述了无环酯和二酯的DIBALH还原乙酰化的优化方案。这种还原乙酰化过程允许各种各样的酯以良好至优异的产率转化为相应的α-乙酰氧基醚。发现在弱酸性条件下,许多α-乙酰氧基醚可进一步还原为相应的醚。这种净两步酯脱氧是一种有吸引力的替代经典的威廉姆森合成某些醚。
An optimized protocol for the DIBALH reductive acetylation of acyclic esters and diesters is described. This reductive acetylation procedure allows a wide variety of esters to be converted into the corresponding α-acetoxy ethers in good to excellent yields. It was found that, under mild acidic conditions, many α-acetoxy ethers can be further reduced to the corresponding ethers. This net two-step ester deoxygenation is an attractive alternative to the classical Williamson synthesis for certain ethers.