Revisiting the Julia-Colonna enantioselective epoxidation: supramolecular catalysis in water

被引：19

作者：

Berube, Christopher ^{[1
,2
]}

Barbeau, Xavier ^{[2
,3
]}

Lague, Patrick ^{[2
,3
]}

Voyer, Normand ^{[1
,2
]}

机构：

[1] Univ Laval, Dept Chim, Fac Sci & Genie, 1045 Ave Med, Quebec City, PQ G1V OA6, Canada

[2] Univ Laval, PROTEO, Fac Sci & Genie, 1045 Ave Med, Quebec City, PQ G1V OA6, Canada

[3] Univ Laval, Dept Biochim Microbiol & Bioinformat, Fac Sci & Genie, 1045 Ave Med, Quebec City, PQ G1V OA6, Canada

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 37期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ALPHA-AMINO-ACIDS; POLY-L-LEUCINE; ASYMMETRIC EPOXIDATION; ALPHA; BETA-UNSATURATED KETONES; ORGANIC-SYNTHESIS; POLYAMINO-ACIDS; SYNTHETIC ENZYMES; GREEN CHEMISTRY; STEREOSELECTIVE EPOXIDATION; TRIPHASE SYSTEM;

D O I：

10.1039/c7cc01168g

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

We describe an efficient epoxidation process leading to chiral epoxyketones using the reusable homo-oligopeptide poly-L-leucine (PLL) in pure water, without any organic co-solvent. A range of substituted epoxyketones can be accessed with good conversions and high enantioselectivities. Based on the experimental results and computational studies, we propose a mechanism that demonstrates the importance of both the alpha-helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.

引用

收藏

页码：5099 / 5102

页数：4

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