A General Synthesis of Bis-α-acyloxy-1,4-and -1,5-diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols

被引：19

作者：

Piccialli, Vincenzo ^{[1
]}

D'Errico, Stefano ^{[2
]}

Borbone, Nicola ^{[2
]}

Oliviero, Giorgia ^{[2
]}

Centore, Roberto ^{[1
]}

Zaccaria, Sabrina ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy

[2] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 09期

关键词：

Synthetic methods; Oxidation; Ring-opening; Cyclization; Nitrogen heterocycles; Oxygen heterocycles; ALPHA-ACETOXY KETONES; ANNONACEOUS ACETOGENINS; CYCLIZATION; 1,5-DIENES; TETROXIDE; BENZOYLOXYLATION; OXYACYLATION; 1,6-DIENES; CHEMISTRY; ACETATE;

D O I：

10.1002/ejoc.201201554

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first general synthesis of bis-alpha-acyloxy-1,4- and -1,5-diketones has been accomplished in a catalytic oxidative opening of bis-acylated THF and THP (tetrahydropyran) diols, which were synthesised by osmium- or ruthenium-catalysed oxidative cyclisation of 1,5- and 1,6-dienes. The overall sequence corresponds to the regioselective double ketoacylox-ylation of the starting diene. The synthesised bis-alpha-acyloxy-1,5-dicarbonyl compounds have been transformed into pyridine-based oxido pincer ligands or pyrazinedimethanol substances, leading to the discovery of unprecedented aromatisation routes.

引用

页码：1781 / 1789

页数：9

共 52 条

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