Kinetic resolution displaying zeroth order dependence on substrate consumption: Copper-catalyzed asymmetric alcoholysis of azlactones

被引：29

作者：

Tokunaga, M ^{[1
]}

Kiyosu, J

Obora, Y

Tsuji, Y

机构：

[1] Hokkaido Univ, SORST, Grad Sch Sci, Catalysis Res Ctr, Sapporo, Hokkaido 0010021, Japan

[2] Hokkaido Univ, SORST, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0010021, Japan

[3] JST, CREST, Sapporo, Hokkaido 0010021, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 13期

关键词：

D O I：

10.1021/ja058112j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetic resolution of 4-alkyl-2-aryl-5-oxo-4,5-dihydrooxazole-4-carboxylic acid esters (azlactones 1) were achieved by copper-DTBM-SEGPHOS catalyzed alcoholysis reaction with good selectivity (12 examples). Variation of ee of unreacted substrates 1 and products 2 with conversion was found to follow the theoretical line of zeroth-order kinetic resolution, for which the selectivity profiles and graphical analysis were presented for the first time. The efficiency of resolution in zeroth-order reaction is higher than first-order reaction. For example, the reaction with la afforded (S)-1a (99% ee) and (R)-2a (74% ee) at 57% conversion, where the k(ret) values were calculated to be 6.7 as zeroth-order kinetic resolution and 37 as first-order kinetic resolution.

引用

页码：4481 / 4486

页数：6

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