Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent

被引：26

作者：

Dang, Hang T. ^{[1
]}

Nguyen, Vu T. ^{[1
]}

Nguyen, Viet D. ^{[1
]}

Arman, Hadi D. ^{[1
]}

Larionov, Oleg V. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 19期

关键词：

CATALYZED ASYMMETRIC HYDROGENATION; DABCO-BIS(SULFUR DIOXIDE); STEREOSELECTIVE-SYNTHESIS; POTASSIUM METABISULFITE; FLUORINATED ALCOHOLS; BORONIC ACIDS; DIELS-ALDER; METAL-FREE; CHEMISTRY; HALIDES;

D O I：

10.1039/c8ob00745d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present herein an efficient and practical method for a gram scale synthesis of 3-sulfolenes using sodium metabisulfite as a safe, inexpensive, and easy to handle sulfur dioxide equivalent. Diversely-substituted 3-sulfolenes can be prepared by reacting a variety of 1,3-dienes or allylic alcohols with sodium metabisulfite in aqueous hexafluoroisopropanol (HFIP) or in aqueous methanol in the presence of potassium hydrogen sulfate. Advantageously, the method enables conversion of allylic alcohols directly to 3-sulfolenes, bypassing intermediate 1,3-dienes.

引用

页码：3605 / 3609

页数：5

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