Primary Alkylboronic Acids as Highly Active Catalysts for the Dehydrative Amide Condensation of α-Hydroxycarboxylic Acids

被引：79

作者：

Yamashita, Risa ^{[1
]}

Sakakura, Akira ^{[2
]}

Ishihara, Kazuaki ^{[1
,3
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[2] Okayama Univ, Sch Nat Sci & Technol, Kita Ku, Okayama 7008530, Japan

[3] JST, CREST, Tokyo, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 14期

关键词：

BETA-ADRENERGIC RECEPTORS; CARBOXYLIC-ACIDS; BORIC-ACID; BOND FORMATION; CARDIOTONIC AGENT; ENANTIOSELECTIVE SYNTHESIS; DENOPAMINE TA-064; AMIDATION; AFFINITY; AMINES;

D O I：

10.1021/ol401537f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Primary alkylboronic acids such as methyl boronic acid and butylboronic acid are highly active catalysts for the dehydrative amide condensation of alpha-hydroxycarboxylic acids. The catalytic activities of these primary alkylboronic acids are much higher than those of the previously reported arylboronic acids. The present method was easily applied to a large-scale synthesis, and 14 g of an amide was obtained in a single reaction.

引用

页码：3654 / 3657

页数：4

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