Diastereoselective Synthesis of 2-(1,3-Dioxolanes-4-yl)-4H-pyran-4-ones from 2-Diazo-3,5-dioxo-6-ynoates (sulfones) and Aldehydes Based on Tandem Cyclization-Cycloaddition Strategy

被引：11

作者：

Zhang, Jianfang ^{[1
,2
]}

Deng, Guisheng ^{[1
,2
,3
]}

Wang, Jianbo ^{[3
]}

机构：

[1] Hunan Normal Univ, Minist Educ China, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China

[2] Hunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Hunan, Peoples R China

[3] Peking Univ, BNLMS, Beijing 100871, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 24期

基金：

中国国家自然科学基金;

关键词：

Gamma-Pyranone; Cycloaddition; 1; 3-dioxolanes; Tandem cyclization; CARBONYL YLIDE FORMATION; GAMMA-PYRONES; 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE REVERSAL; DERIVATIVES; DIOXOLANES; CARBENOIDS; 4-PYRONE; GOLD;

D O I：

10.1002/ejoc.201900545

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In AgSbF6/Rh-2(OAc)(4)/DCM system, two-component reaction of 2-diazo-3,5-dioxo-6-ynoates (sulfones) and two equivalent of aldehydes provided easy access to 2-(1,3-dioxolanes-4-yl)-4H-pyran-4-ones. This represents the first method for generating the novel heterocyclic compounds. A possible mechanism is proposed to explain this result. The most significant features of the tandem cyclization are simple procedure, mild conditions and high diastereoselectivity.

引用

页码：3979 / 3986

页数：8

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