An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: A powerful and convenient mixed anhydride method promoted by basic catalysts

被引：366

作者：

Shiina, I ^{[1
]}

Kubota, M ^{[1
]}

Oshiumi, H ^{[1
]}

Hashizume, M ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 06期

关键词：

D O I：

10.1021/jo030367x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine by the promotion of a basic catalyst such as 4-(dimethylamino)pyridine. A variety of lactones are also prepared in high yields at room temperature from the corresponding w-hydroxycarboxylic acids with use of 2-methyl-6-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. A similar reaction occurs with triethylamine when using a catalytic amount of 4-(dimethylamino)pyridine 1-oxide as an effective promoter for the intramolecular condensation reaction. These methods are successfully applied to the synthesis of erythro-aleuritic acid lactone and an eight-membered-ring lactone moiety of octalactins A and B. The efficiency of the cyclizations is compared to those of other reported lactonizations.

引用

页码：1822 / 1830

页数：9

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