Development of a One-Pot Tandem Reaction Combining Ruthenium-Catalyzed Alkene Metathesis and Enantioselective Enzymatic Oxidation To Produce Aryl Epoxides

被引：62

作者：

Denard, Carl A. ^{[1
]}

Bartlett, Mark J. ^{[2
]}

Wang, Yajie ^{[1
]}

Lu, Lu ^{[3
]}

Hartwig, John F. ^{[2
]}

Zhao, Huimin ^{[1
,4
]}

机构：

[1] Univ Illinois, Dept Chem & Biomol Engn, Urbana, IL 61801 USA

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[3] Univ Illinois, Dept Mol & Cellular Biol, Urbana, IL 61801 USA

[4] Univ Illinois, Dept Chem Biochem & Bioengn, Carl R Woese Inst Genom Biol, Urbana, IL 61801 USA

来源：

ACS CATALYSIS | 2015年 / 5卷 / 06期

基金：

美国国家科学基金会;

关键词：

chemo-enzymatic catalysis; cytochrome P450; organometallic catalysis; biocatalysis; tandem catalysis; olefin metathesis; DIRECTED EVOLUTION; PHOSPHITE DEHYDROGENASE; OLEFIN METATHESIS; CYTOCHROME P450BM-3; SCREENING SYSTEM; EPOXIDATION; METAL; REGENERATION; BIOCATALYSTS; COMBINATION;

D O I：

10.1021/acscatal.5b00533

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We report the development of a tandem chemoenzymatic transformation that combines alkene metathesis with enzymatic epoxidation to provide aryl epoxides. The development of this one-pot reaction required substantial protein and reaction engineering to improve both selectivity and catalytic activity. Ultimately, this reaction converts a mixture of alkenes into a single epoxide product in high enantioselectivity and moderate yields and illustrates both the challenges and benefits of tandem catalysis combining organometallic and enzymatic systems.

引用

页码：3817 / 3822

页数：6

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