Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation
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DOI:
10.1016/j.tetasy.2012.05.004
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发表时间:
2012-05-15
影响因子:
--
通讯作者:
Andrade, Leandro H.
Andrade, Leandro H.
中科院分区:
其他
文献类型:
--
作者:
Brondani, Patricia B.;Dudek, Hanna;Andrade, Leandro H.

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研究了Baeyer-Villiger单加氧酶对几种手性含硼化合物的碳-硼键对映选择性氧化反应。PAMO和M446 G PAMO方便地将1-苯乙基硼酸酯氧化成相应的1-(苯基)乙醇(ee = 82-91%)。环丙基硼酸酯也被氧化,但没有对映选择性。β-硼基羧酸酯不被任何BVMO氧化。(C)2012爱思唯尔有限公司保留所有权利。
The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.